The Experts below are selected from a list of 318 Experts worldwide ranked by ideXlab platform
Alexander Dömling - One of the best experts on this subject based on the ideXlab platform.
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Tetrazoles via Multicomponent Reactions
Chemical Reviews, 2019Co-Authors: Constantinos G. Neochoritis, Ting Zhao, Alexander DömlingAbstract:Tetrazole derivatives are a prime class of heterocycles, very important to medicinal chemistry and drug design due to not only their bioisosterism to carboxylic acid and amide moieties but also to their metabolic stability and other beneficial physicochemical properties. Although more than 20 FDA-approved drugs contain 1H- or 2H-tetrazole substituents, their exact binding mode, structural biology, 3D conformations, and in general their chemical behavior is not fully understood. Importantly, multicomponent reaction (MCR) chemistry offers convergent access to multiple tetrazole scaffolds providing the three important elements of novelty, diversity, and complexity, yet MCR pathways to Tetrazoles are far from completely explored. Here, we review the use of multicomponent reactions for the preparation of substituted tetrazole derivatives. We highlight specific applications and general trends holding therein and discuss synthetic approaches and their value by analyzing scope and limitations, and also enlighten ...
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convergent three component tetrazole synthesis
European Journal of Organic Chemistry, 2016Co-Authors: Ajay L Chandgude, Alexander DömlingAbstract:A microwave-accelerated, simple, and efficient method for the construction of the 1,5-tetrazole scaffold was developed. It comprises a multicomponent reaction of an amine, a carboxylic acid derivative, and an azide source. On the basis of the availability of the archetypical starting materials, this method provided very versatile synthetic access to 1,5-disubstituted Tetrazoles. The usefulness of this method was demonstrated in the synthesis of biologically important fused tetrazole scaffolds and the marketed drug cilostazol.
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α amino acid isosteric α amino Tetrazoles
Chemistry: A European Journal, 2016Co-Authors: T C Zhao, Katarzyna Kurpiewska, Justyna Kalinowskatluścik, Eberhardt Herdtweck, Alexander DömlingAbstract:The synthesis of all 20 common natural proteinogenic and 4 otherα-amino acid-isosteric α-amino Tetrazoles has been accomplished, whereby the carboxyl group is replaced by the isosteric 5-tetrazolyl group. The short process involves the use of the key Ugi tetrazole reaction followed by deprotection chemistries. The tetrazole group is bioisosteric to the carboxylic acid and is widely used in medicinal chemistry and drug design. Surprisingly, several of the common α-amino acid-isosteric α-amino Tetrazoles are unknown up to now. Therefore a rapid synthetic access to this compound class and non-natural derivatives is of high interest to advance the field.
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hydrazine in the ugi tetrazole reaction
Synthesis, 2016Co-Authors: Pravin O Patil, Katarzyna Kurpiewska, Justyna Kalinowskatluścik, Ji Zhang, Alexander DömlingAbstract:We describe the hitherto unknown use of N-Boc-protected hydrazine in the Ugi tetrazole reaction to access a library of highly substituted 5-(hydrazinomethyl)-1-methyl-1H-Tetrazoles. The reaction is very versatile and good to high yielding. A one-pot, two-step procedure is given.
Pavel N. Gaponik - One of the best experts on this subject based on the ideXlab platform.
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Synthesis, properties, and structure of Tetrazoles: Certain achievements and prospects
Russian Journal of Organic Chemistry, 2013Co-Authors: Sergei V. Voitekhovich, Oleg A. Ivashkevich, Pavel N. GaponikAbstract:The review generalizes and systematizes the results of research on the synthesis and properties of tetrazole derivatives obtained in the Belarusian State University within the last decade. The main attention is fixed on important directions in the tetrazole synthesis: the acid-catalyzed N-alkylation, the reactions of primary amines with triethyl orthoformate and sodium azide followed by the heterocyclization of imidoyl azides, and on the transformation of the obtained 1-arylTetrazoles into 1-aryl-5-aminoTetrazoles. The results of quantum-chemical and X-ray investigations as well as aspects of the practical application of Tetrazoles are reviewed.
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Metal derivatives of Tetrazoles
Russian Chemical Reviews, 2006Co-Authors: Pavel N. Gaponik, Sergei V. Voitekhovich, Oleg A. IvashkevichAbstract:Published data on the synthesis, structure, properties and applications of metal derivatives of Tetrazoles are generalised and described systematically. Compounds based on the anionic and neutral tetrazole forms, C- and N-mono- and C,N-disubstituted Tetrazoles are considered.
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Organometallic Tetrazole Derivatives: Preparation and Application to Organic Synthesis
Russian Journal of Organic Chemistry, 2005Co-Authors: Sergei V. Voitekhovich, Pavel N. Gaponik, G. I. KoldobskiiAbstract:The data are integrated and systematized on preparation procedures and application to the organic synthesis of organometallic tetrazole derivatives, including 5-metallated Tetrazoles and Tetrazoles with a metal-carbon bond in a substituent, and also organotin Tetrazoles.
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Selective synthesis of 2-(1-methylvinyl)Tetrazoles
Mendeleev Communications, 1997Co-Authors: Sergei V. Voitekhovich, Pavel N. Gaponik, A. O. KorenAbstract:Hitherto unknown 2-(1-methylvinyl)Tetrazoles have been obtained by regioselective alkylation of tetrazole and 5R-Tetrazoles with 1-halogenopropan-2-ols and 3-bromopropene followed by dehydrohalogenation of the intermediate products.
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Polymers and copolymers based on vinyl Tetrazoles, 2. Alkylation of poly(5-vinyl tetrazole)†
Angewandte Makromolekulare Chemie, 1994Co-Authors: Pavel N. Gaponik, Anatoly I. Lesnikovich, Oleg A. Ivashkevich, Nadejda I. Chernavina, G. T. Sukhanov, Gegel A. GareevAbstract:Alkylation of poly(5-vinyl tetrazole) with dimethyl sulfate and tert-butyl alcohol as well as with alkyl halides RHal (RCH3, C2H5, CH2CHCH2, n-C4H9, t-C4H9) has been studied under various conditions in order to develop a new method of synthesis of tetrazole-containing polymers having a complex of valuable properties. The kinetic study of the process and comparison of isomeric compositions and spectroscopic characteristics (IR, 1H NMR and 13C NMR) of poly(N-alkyl-5-vinyl tetrazole)s synthesized by alkylation of poly(5-vinyl tetrazole) and of those prepared by (co)polymerization of the corresponding vinyl Tetrazoles have been carried out. The alkylation is found to proceed to high conversion extents (up to 99.8%) and enables to obtain a wide variety of polymeric products having the composition, structure and properties very similar to those of homo- and copolymers. Die Alkylierung von Poly(5-vinyltetrazol) mit Dimethylsulfat und tert-Butylalkohol sowie Alkylhalogeniden RHal (RCH3, C2H5, CH2CHCH2, n-C4H9 und t-C4H9) und die Kinetik dieser Reaktion wurden untersucht, um eine neue Herstellungsmethode fur tetrazolhaltige Polymere mit wertvollen Eigenschaften zu entwickeln. Die vergleichenden Untersuchungen uber die isomere Zusammensetzung und die spektroskopischen Daten von Poly(N-alkyl-5-vinyltetrazol)en, die durch die Alkylierung von Poly(5-vinyltetrazol) sowie durch die Copolymerisation der entsprechenden Monomeren hergestellt wurden, wurden mit IR-, 1H-NMR- und 13C-NMR-Spektroskopie durchgefuhrt. Der Alkylierungsumsatz betragt bis zu 99,8%; dadurch konnen polymere Produkte erhalten werden, deren Zusammensetzung, Struktur und Eigenschaften denen der Homo- und Copolymeren sehr ahnlich sind.
Rostislav E. Trifonov - One of the best experts on this subject based on the ideXlab platform.
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6.07 – Tetrazoles
Comprehensive Heterocyclic Chemistry III, 2020Co-Authors: Vladimir A. Ostrovskii, G. I. Koldobskii, Rostislav E. TrifonovAbstract:Tetrazoles were discovered by Bladin over 120 years ago (1885). Since then, tetrazole and its derivatives have attracted interest by their unique structure and extreme characteristics. Especially great activity in this field of chemistry has been observed since 1996. The number of publications and patents on preparation methods, properties, and applications of Tetrazoles grows every year with a higher rate than with respect to other heterocyclic systems. This fact actually reflects the significant achievements in fundamental research and industry in tetrazole chemistry at the end of the twentieth and beginning of the twenty-first centuries. This chapter describes various aspects regarding Tetrazoles: electronic structure, thermodynamic and theoretical problems, including aromaticity, acid–base properties, tautomerism, and also experimental structural methods. Mechanism and kinetics of unimolecular thermal and photochemical reactions of Tetrazoles, molecular rearrangements, etc., are discussed. The reactivity of ring nitrogen and carbon atoms is treated: electrophilic attack at endocyclic nitrogen and carbon atoms, nucleophilic attack at endocyclic carbon, complex formation with metal ions. Considerable attention is paid to the reactivity of substituents attached to the ring nitrogen in neutral Tetrazoles, tetrazolate anions, and tetrazolium cations, and also to the electrophilic and nucleophilic attack at endocyclic carbon. Various possible procedures are described for ring synthesis from acyclic compounds, and also by transformations of other heterocyclic systems. Preferred routes to tetrazole classes are indicated. In all sections of this chapter, attention is focused on new constructive ideas, efficient methods of synthesis and transformation of Tetrazoles, and urgent problems of tetrazole chemistry. In the concluding sections, data are given on important compounds and applications: biologically active substances, drug applications, energetic Tetrazoles, Tetrazoles as promising objects in supramolecular chemistry and nanotechnology, and also as activators of chemical and biochemical reactions, etc.
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Medicinal chemistry of Tetrazoles
Russian Chemical Bulletin, 2020Co-Authors: Vladimir A. Ostrovskii, Rostislav E. Trifonov, E. A. PopovaAbstract:Properties of responsible for biological activity Tetrazoles are considered. Examples are given of active pharmaceutical ingredients of modern drugs containing the tetrazole ring in the molecular structure. New publications on the synthesis and investigations of biological activity of promising tetrazole-containing compounds are cited.
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Tetrazole Derivatives as Promising Anticancer Agents
Anti-cancer Agents in Medicinal Chemistry, 2018Co-Authors: E. A. Popova, Aleksandra V. Protas, Rostislav E. TrifonovAbstract:Tetrazole cycle is a promising pharmacophore fragment frequently used in the development of novel drugs. This moiety is a stable, practically non-metabolized bioisosteric analog of carboxylic, cis-amide, and other functional groups. Over recent 10–15 years, various isomeric forms of tetrazole (NH-unsubstituted, 1H-1-substituted, and 2H-2-substituted Tetrazoles) have been successfully used in the design of promising anticancer drugs. Coordination compounds of transition metals containing Tetrazoles as ligands, semisynthetic tetrazolyl derivatives of natural compounds (biogenic acids, peptides, steroids, combretastatin, etc.), 5-oxo and 5-thioTetrazoles, and some other related compounds have been recognized as promising antineoplastic agents. This review presents a comprehensive analysis of modern approaches to synthesis of these tetrazole derivatives as well as their biological (anticancer) properties. The most promising structure types of Tetrazoles to be used as anticancer agents have been picked out.
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alkylation of 5 substituted nh Tetrazoles by alcohols in the superacid cf3so3h
Tetrahedron Letters, 2015Co-Authors: Anna D Lisakova, Vladimir A. Ostrovskii, Rostislav E. Trifonov, Dmitry S Ryabukhin, Aleksander V VasilyevAbstract:Abstract Reactions of 5-substituted NH-Tetrazoles with alcohols in the superacid CF 3 SO 3 H have been studied. Both the structure of the tetrazole and the nature of alcohol were found to dramatically influence the selectivity of the reaction and yields of products. Tetrazoles bearing phenyl, electron-donating aryl, or benzyl groups at the 5-position, have been alkylated using various alcohols (including MeOH and EtOH) in CF 3 SO 3 H upon heating at 60 °C for 0.3–12 h to afford 2-alkyl-2 H -Tetrazoles in 30–98% yields.
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synthesis of tetrazole containing c phosphonoacetamidines
Synlett, 2015Co-Authors: Nataly I Svintsitskaya, Albina V Dogadina, Rostislav E. TrifonovAbstract:Addition of 5-substituted Tetrazoles to dialkyl 2-( N - tert -butyl- or N -adamantyl)iminovinylphosphonates proceeds regioselectively to yield novel tetrazole-containing phosphonoacetamidines – 2-[( N - tert -butyl- or N -adamantyl)imino-2-(tetrazolyl)ethyl]phosphonic acid dialkyl esters – with good yields. The reactions occur via nucleophilic attack of the tetrazole N-1 atom at the C=C bond.
Vladimir A. Ostrovskii - One of the best experts on this subject based on the ideXlab platform.
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6.07 – Tetrazoles
Comprehensive Heterocyclic Chemistry III, 2020Co-Authors: Vladimir A. Ostrovskii, G. I. Koldobskii, Rostislav E. TrifonovAbstract:Tetrazoles were discovered by Bladin over 120 years ago (1885). Since then, tetrazole and its derivatives have attracted interest by their unique structure and extreme characteristics. Especially great activity in this field of chemistry has been observed since 1996. The number of publications and patents on preparation methods, properties, and applications of Tetrazoles grows every year with a higher rate than with respect to other heterocyclic systems. This fact actually reflects the significant achievements in fundamental research and industry in tetrazole chemistry at the end of the twentieth and beginning of the twenty-first centuries. This chapter describes various aspects regarding Tetrazoles: electronic structure, thermodynamic and theoretical problems, including aromaticity, acid–base properties, tautomerism, and also experimental structural methods. Mechanism and kinetics of unimolecular thermal and photochemical reactions of Tetrazoles, molecular rearrangements, etc., are discussed. The reactivity of ring nitrogen and carbon atoms is treated: electrophilic attack at endocyclic nitrogen and carbon atoms, nucleophilic attack at endocyclic carbon, complex formation with metal ions. Considerable attention is paid to the reactivity of substituents attached to the ring nitrogen in neutral Tetrazoles, tetrazolate anions, and tetrazolium cations, and also to the electrophilic and nucleophilic attack at endocyclic carbon. Various possible procedures are described for ring synthesis from acyclic compounds, and also by transformations of other heterocyclic systems. Preferred routes to tetrazole classes are indicated. In all sections of this chapter, attention is focused on new constructive ideas, efficient methods of synthesis and transformation of Tetrazoles, and urgent problems of tetrazole chemistry. In the concluding sections, data are given on important compounds and applications: biologically active substances, drug applications, energetic Tetrazoles, Tetrazoles as promising objects in supramolecular chemistry and nanotechnology, and also as activators of chemical and biochemical reactions, etc.
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Medicinal chemistry of Tetrazoles
Russian Chemical Bulletin, 2020Co-Authors: Vladimir A. Ostrovskii, Rostislav E. Trifonov, E. A. PopovaAbstract:Properties of responsible for biological activity Tetrazoles are considered. Examples are given of active pharmaceutical ingredients of modern drugs containing the tetrazole ring in the molecular structure. New publications on the synthesis and investigations of biological activity of promising tetrazole-containing compounds are cited.
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alkylation of 5 substituted nh Tetrazoles by alcohols in the superacid cf3so3h
Tetrahedron Letters, 2015Co-Authors: Anna D Lisakova, Vladimir A. Ostrovskii, Rostislav E. Trifonov, Dmitry S Ryabukhin, Aleksander V VasilyevAbstract:Abstract Reactions of 5-substituted NH-Tetrazoles with alcohols in the superacid CF 3 SO 3 H have been studied. Both the structure of the tetrazole and the nature of alcohol were found to dramatically influence the selectivity of the reaction and yields of products. Tetrazoles bearing phenyl, electron-donating aryl, or benzyl groups at the 5-position, have been alkylated using various alcohols (including MeOH and EtOH) in CF 3 SO 3 H upon heating at 60 °C for 0.3–12 h to afford 2-alkyl-2 H -Tetrazoles in 30–98% yields.
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6 07 Tetrazoles
Reference Module in Chemistry Molecular Sciences and Chemical Engineering#R##N#Comprehensive Heterocyclic Chemistry III, 2008Co-Authors: Vladimir A. Ostrovskii, G. I. Koldobskii, Rostislav E. TrifonovAbstract:Tetrazoles were discovered by Bladin over 120 years ago (1885). Since then, tetrazole and its derivatives have attracted interest by their unique structure and extreme characteristics. Especially great activity in this field of chemistry has been observed since 1996. The number of publications and patents on preparation methods, properties, and applications of Tetrazoles grows every year with a higher rate than with respect to other heterocyclic systems. This fact actually reflects the significant achievements in fundamental research and industry in tetrazole chemistry at the end of the twentieth and beginning of the twenty-first centuries. This chapter describes various aspects regarding Tetrazoles: electronic structure, thermodynamic and theoretical problems, including aromaticity, acid–base properties, tautomerism, and also experimental structural methods. Mechanism and kinetics of unimolecular thermal and photochemical reactions of Tetrazoles, molecular rearrangements, etc., are discussed. The reactivity of ring nitrogen and carbon atoms is treated: electrophilic attack at endocyclic nitrogen and carbon atoms, nucleophilic attack at endocyclic carbon, complex formation with metal ions. Considerable attention is paid to the reactivity of substituents attached to the ring nitrogen in neutral Tetrazoles, tetrazolate anions, and tetrazolium cations, and also to the electrophilic and nucleophilic attack at endocyclic carbon. Various possible procedures are described for ring synthesis from acyclic compounds, and also by transformations of other heterocyclic systems. Preferred routes to tetrazole classes are indicated. In all sections of this chapter, attention is focused on new constructive ideas, efficient methods of synthesis and transformation of Tetrazoles, and urgent problems of tetrazole chemistry. In the concluding sections, data are given on important compounds and applications: biologically active substances, drug applications, energetic Tetrazoles, Tetrazoles as promising objects in supramolecular chemistry and nanotechnology, and also as activators of chemical and biochemical reactions, etc.
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Linear polynuclear tetrazole-containing compounds
Russian Journal of Organic Chemistry, 2004Co-Authors: S. E. Morozova, Andrei Valerievich KOMISSAROV, K. A. Esikov, V. Yu. Zubarev, Aleksandrovich Aleksandr Malin, Vladimir A. OstrovskiiAbstract:Linear polynuclear tetrazole-containing compounds were synthesized. Alkylation of 5-[ω-(5-phenyl-2-tetrazolyl)alkyl]Tetrazoles with ethyl bromoacetate and chloroacetamide gave the corresponding esters and amides. Treatment of the latter with tetrachlorosilane-sodium azide afforded compounds containing three tetrazole rings linked through polymethylene bridges. Acid ionization constants of the products possessing an NH-tetrazole ring (pKa = 2.9–3.2) and the corresponding carboxylic acids (pKa = 2.9–3.1) in aqueous methanol were determined by potentiometric titration.
G. I. Koldobskii - One of the best experts on this subject based on the ideXlab platform.
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6.07 – Tetrazoles
Comprehensive Heterocyclic Chemistry III, 2020Co-Authors: Vladimir A. Ostrovskii, G. I. Koldobskii, Rostislav E. TrifonovAbstract:Tetrazoles were discovered by Bladin over 120 years ago (1885). Since then, tetrazole and its derivatives have attracted interest by their unique structure and extreme characteristics. Especially great activity in this field of chemistry has been observed since 1996. The number of publications and patents on preparation methods, properties, and applications of Tetrazoles grows every year with a higher rate than with respect to other heterocyclic systems. This fact actually reflects the significant achievements in fundamental research and industry in tetrazole chemistry at the end of the twentieth and beginning of the twenty-first centuries. This chapter describes various aspects regarding Tetrazoles: electronic structure, thermodynamic and theoretical problems, including aromaticity, acid–base properties, tautomerism, and also experimental structural methods. Mechanism and kinetics of unimolecular thermal and photochemical reactions of Tetrazoles, molecular rearrangements, etc., are discussed. The reactivity of ring nitrogen and carbon atoms is treated: electrophilic attack at endocyclic nitrogen and carbon atoms, nucleophilic attack at endocyclic carbon, complex formation with metal ions. Considerable attention is paid to the reactivity of substituents attached to the ring nitrogen in neutral Tetrazoles, tetrazolate anions, and tetrazolium cations, and also to the electrophilic and nucleophilic attack at endocyclic carbon. Various possible procedures are described for ring synthesis from acyclic compounds, and also by transformations of other heterocyclic systems. Preferred routes to tetrazole classes are indicated. In all sections of this chapter, attention is focused on new constructive ideas, efficient methods of synthesis and transformation of Tetrazoles, and urgent problems of tetrazole chemistry. In the concluding sections, data are given on important compounds and applications: biologically active substances, drug applications, energetic Tetrazoles, Tetrazoles as promising objects in supramolecular chemistry and nanotechnology, and also as activators of chemical and biochemical reactions, etc.
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Tetrazoles: LII. Synthesis of functionally substituted Tetrazoles from benzene-1,3,5-tricarboxylic acid derivatives
Russian Journal of Organic Chemistry, 2008Co-Authors: M. V. Zatsepina, T. V. Artamonova, G. I. KoldobskiiAbstract:N,N′,N″-Triarylbenzene-1,3-5-tricarboximidoyl chlorides reacted with sodium azide under conditions of phase-transfer catalysis to give functionally substituted Tetrazoles whose subsequent functionalization led to complex heterocyclic structures which may be regarded as first-generation tetrazole-containing dendrimers.
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6 07 Tetrazoles
Reference Module in Chemistry Molecular Sciences and Chemical Engineering#R##N#Comprehensive Heterocyclic Chemistry III, 2008Co-Authors: Vladimir A. Ostrovskii, G. I. Koldobskii, Rostislav E. TrifonovAbstract:Tetrazoles were discovered by Bladin over 120 years ago (1885). Since then, tetrazole and its derivatives have attracted interest by their unique structure and extreme characteristics. Especially great activity in this field of chemistry has been observed since 1996. The number of publications and patents on preparation methods, properties, and applications of Tetrazoles grows every year with a higher rate than with respect to other heterocyclic systems. This fact actually reflects the significant achievements in fundamental research and industry in tetrazole chemistry at the end of the twentieth and beginning of the twenty-first centuries. This chapter describes various aspects regarding Tetrazoles: electronic structure, thermodynamic and theoretical problems, including aromaticity, acid–base properties, tautomerism, and also experimental structural methods. Mechanism and kinetics of unimolecular thermal and photochemical reactions of Tetrazoles, molecular rearrangements, etc., are discussed. The reactivity of ring nitrogen and carbon atoms is treated: electrophilic attack at endocyclic nitrogen and carbon atoms, nucleophilic attack at endocyclic carbon, complex formation with metal ions. Considerable attention is paid to the reactivity of substituents attached to the ring nitrogen in neutral Tetrazoles, tetrazolate anions, and tetrazolium cations, and also to the electrophilic and nucleophilic attack at endocyclic carbon. Various possible procedures are described for ring synthesis from acyclic compounds, and also by transformations of other heterocyclic systems. Preferred routes to tetrazole classes are indicated. In all sections of this chapter, attention is focused on new constructive ideas, efficient methods of synthesis and transformation of Tetrazoles, and urgent problems of tetrazole chemistry. In the concluding sections, data are given on important compounds and applications: biologically active substances, drug applications, energetic Tetrazoles, Tetrazoles as promising objects in supramolecular chemistry and nanotechnology, and also as activators of chemical and biochemical reactions, etc.
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Drugs in the tetrazole series. (Review)
Chemistry of Heterocyclic Compounds, 2007Co-Authors: L. V. Myznikov, Alexandr Hrabálek, G. I. KoldobskiiAbstract:Data on drugs of the tetrazole series published over the last decade are reviewed. The use of Tetrazoles as isosteric substituents of various functional groups is examined.
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Strategies and prospects in functionalization of Tetrazoles
Russian Journal of Organic Chemistry, 2006Co-Authors: G. I. KoldobskiiAbstract:The review summarizes the methods of functionalization of Tetrazoles, which were reported from 2001 to mid 2005, and analyzes main strategies in the development of this field of tetrazole chemistry.
