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Ikyon Kim - One of the best experts on this subject based on the ideXlab platform.
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Expansion of diazepine heterocyclic chemical space via sequential Knoevenagel condensation-intramolecular aza-Wittig reaction: 2-acyl-4-aryl-5H-pyrrolo[1,2-d][1,4]diazepines.
Organic & biomolecular chemistry, 2020Co-Authors: Anuradha Dagar, Ikyon KimAbstract:A highly efficient synthetic route to a new 1,4-diazepene skeleton, 2-acyl-4-aryl-5H-pyrrolo[1,2-d][1,4]diazepine, was established where Knoevenagel condensation of readily available two fragments, N-substituted pyrrole-2-carboxaldehyde and α-azidoketone, followed by intramolecular aza-Wittig reaction under Staudinger Azide Reduction conditions permitted facile access to a poly-substituted 1,4-diazepine ring system for the first time. Successful application of this protocol to construct new 1-alkoxy-3-acylisoquinolines and 1-alkoxy-3-acyl-β-carbolines is also demonstrated.
Anuradha Dagar - One of the best experts on this subject based on the ideXlab platform.
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Expansion of diazepine heterocyclic chemical space via sequential Knoevenagel condensation-intramolecular aza-Wittig reaction: 2-acyl-4-aryl-5H-pyrrolo[1,2-d][1,4]diazepines.
Organic & biomolecular chemistry, 2020Co-Authors: Anuradha Dagar, Ikyon KimAbstract:A highly efficient synthetic route to a new 1,4-diazepene skeleton, 2-acyl-4-aryl-5H-pyrrolo[1,2-d][1,4]diazepine, was established where Knoevenagel condensation of readily available two fragments, N-substituted pyrrole-2-carboxaldehyde and α-azidoketone, followed by intramolecular aza-Wittig reaction under Staudinger Azide Reduction conditions permitted facile access to a poly-substituted 1,4-diazepine ring system for the first time. Successful application of this protocol to construct new 1-alkoxy-3-acylisoquinolines and 1-alkoxy-3-acyl-β-carbolines is also demonstrated.
I. Namboothiri - One of the best experts on this subject based on the ideXlab platform.
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SAEGUSA Enone Synthesis to SZARVASY–SCHÖPF Carbomethoxylation
Organic Syntheses Based on Name Reactions, 2012Co-Authors: Alfred Hassner, I. NamboothiriAbstract:This article contains brief overviews, mechanisms and practical details for organic synthesis named reactions and processes beginning with the letter ‘S’. Reactions included in this section are: SAEGUSA Enone Synthesis; SAKURAI Allylation via Allylsilanes; SANDMEYER Isatin Synthesis; SANDMEYER–GATTERMANN Aromatic Substitution; SANGER Amino Acid Labeling Reagent; SARETT Cr Oxidizing Reagent; SCHEINER Aziridine Triazoline Synthesis; SCHENCK Allylic Oxidation; SCHIEMANN Aromatic Fluorination; SCHMIDT Rearrangement via Azides; SCHMITZ Diaziridine Synthesis; SCHOLL Polyaromatic Synthesis; SCHOLLKOPF Amino Acid Synthesis; SCHOLLKOPF–BARTON–ZARD Pyrrole Synthesis; SCHOLTZ Indolizine Synthesis; SCHOTTEN–BAUMANN Alcohol and Amine Acylation; SCHWARTZ Hydrozirconation; SCHWEIZER Allylamine Synthesis; SCHWEIZER Allenyl Azine Rearrangement; SCHWESINGER Phosphazene Bases; SEEBACH Chiral Oxazolidinones; SEEBACH–BECK TADDOL Reagent; SEEBACH–COREY Dithiane Reagents; SEMMLER–WOLFF Oxime Aromatization; SEYFERTH Acyllithium Reagent; SEYFERTH Dihalocarbene Reagent; SEYFERTH – GILBERT Diazoalkane Reagent; SHAPIRO Olefination via Tosylhydrazones; SHARPLESS Allylic Amination; SHARPLESS Asymmetric Dihydroxylation; SHARPLESS Asymmetric Epoxidation; SHEEHAN Carbodiimide Coupling Reagent; SHERADSKY – ENDO Hetero-Cope Rearrangement; SHESTAKOV Hydrazino Acid Synthesis; SHEVERDINA–KOCHESHKOV Electrophilic Amination; SHIBASAKI Ti–N Complex; SIEGRIST Stilbene Synthesis; SIMCHEN Azaheterocycle Synthesis; SIMMONS – SMITH Cyclopropanation; SIMONIS Benzopyrone Synthesis; SKATTEBOL Vinyldihalocyclopropane Rearrangement; SKRAUP Quinoline Synthesis; SMILES Aromatic Rearrangement; SMITH–MIDDLETON–ROZEN Fluorination; SNIECKUS Carbamate Rearrangement; SODERQUIST Boranes; SOMMELET Aldehyde Synthesis; SOMMELET Ammonium Ylide Rearrangement; SONN – MULLER Aldehyde Synthesis; SONOGASHIRA Acetylene Coupling; SOULA Phase Transfer Catalyst; SPECKAMP Acyliminium Ions; SPENGLER–PFANNENSTIEL Sugar Oxidation; SREBNIK–QUNTAR Cyclopropyl Phosphonates; STAAB Carbonylimidazole; Staudinger Azide Reduction; Staudinger Ketene Cycloadditions; Staudinger – PFENNINGER Thiirane Dioxide Synthesis; STEGLICH – HASSNER Direct Alcohol Esterification; STEPHEN Aldehyde Synthesis; STEPHENS–CASTRO Acetylene Coupling; STETTER 1,4-Dicarbonyl Synthesis; STEVENS Ammonium Ylide Rearrangement; STIEGLITZ N -Haloamine Rearrangement; STILES–SISTI Grignard Formylation; STILLE Carbonyl Synthesis; STILLE Cross Coupling; STILL–GENNARI Z-Olefin Synthesis; STOBBE Succinic Ester Condensation; STOLTZ Asymmetric Ketone α-Allylation; STORK–HUNIG Cyanohydrin Alkylation; STORK Enamine Alkylation; STORK Radical Cyclization; STORK Reductive Cyclization; STORK–HAUSER Aminonitrile Alkylation; STORK–ZHAO Z -Iodo-olefin Synthesis; STORY Macrocycle Synthesis; STRECKER Aminoacid Synthesis; STRYKER Regioselective Reduction; SUAREZ Photochemical lodo Functionalization; SUZUKI Aromatic Nitration; SUZUKI Selective Nitrile Reduction; SUZUKI–MIYAURA C C Coupling; SWARTS Fluoroalkane Synthesis; SWERN Alcohol Oxidation; SZARVASY–SCHOPF Carbomethoxylation
Alfred Hassner - One of the best experts on this subject based on the ideXlab platform.
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SAEGUSA Enone Synthesis to SZARVASY–SCHÖPF Carbomethoxylation
Organic Syntheses Based on Name Reactions, 2012Co-Authors: Alfred Hassner, I. NamboothiriAbstract:This article contains brief overviews, mechanisms and practical details for organic synthesis named reactions and processes beginning with the letter ‘S’. Reactions included in this section are: SAEGUSA Enone Synthesis; SAKURAI Allylation via Allylsilanes; SANDMEYER Isatin Synthesis; SANDMEYER–GATTERMANN Aromatic Substitution; SANGER Amino Acid Labeling Reagent; SARETT Cr Oxidizing Reagent; SCHEINER Aziridine Triazoline Synthesis; SCHENCK Allylic Oxidation; SCHIEMANN Aromatic Fluorination; SCHMIDT Rearrangement via Azides; SCHMITZ Diaziridine Synthesis; SCHOLL Polyaromatic Synthesis; SCHOLLKOPF Amino Acid Synthesis; SCHOLLKOPF–BARTON–ZARD Pyrrole Synthesis; SCHOLTZ Indolizine Synthesis; SCHOTTEN–BAUMANN Alcohol and Amine Acylation; SCHWARTZ Hydrozirconation; SCHWEIZER Allylamine Synthesis; SCHWEIZER Allenyl Azine Rearrangement; SCHWESINGER Phosphazene Bases; SEEBACH Chiral Oxazolidinones; SEEBACH–BECK TADDOL Reagent; SEEBACH–COREY Dithiane Reagents; SEMMLER–WOLFF Oxime Aromatization; SEYFERTH Acyllithium Reagent; SEYFERTH Dihalocarbene Reagent; SEYFERTH – GILBERT Diazoalkane Reagent; SHAPIRO Olefination via Tosylhydrazones; SHARPLESS Allylic Amination; SHARPLESS Asymmetric Dihydroxylation; SHARPLESS Asymmetric Epoxidation; SHEEHAN Carbodiimide Coupling Reagent; SHERADSKY – ENDO Hetero-Cope Rearrangement; SHESTAKOV Hydrazino Acid Synthesis; SHEVERDINA–KOCHESHKOV Electrophilic Amination; SHIBASAKI Ti–N Complex; SIEGRIST Stilbene Synthesis; SIMCHEN Azaheterocycle Synthesis; SIMMONS – SMITH Cyclopropanation; SIMONIS Benzopyrone Synthesis; SKATTEBOL Vinyldihalocyclopropane Rearrangement; SKRAUP Quinoline Synthesis; SMILES Aromatic Rearrangement; SMITH–MIDDLETON–ROZEN Fluorination; SNIECKUS Carbamate Rearrangement; SODERQUIST Boranes; SOMMELET Aldehyde Synthesis; SOMMELET Ammonium Ylide Rearrangement; SONN – MULLER Aldehyde Synthesis; SONOGASHIRA Acetylene Coupling; SOULA Phase Transfer Catalyst; SPECKAMP Acyliminium Ions; SPENGLER–PFANNENSTIEL Sugar Oxidation; SREBNIK–QUNTAR Cyclopropyl Phosphonates; STAAB Carbonylimidazole; Staudinger Azide Reduction; Staudinger Ketene Cycloadditions; Staudinger – PFENNINGER Thiirane Dioxide Synthesis; STEGLICH – HASSNER Direct Alcohol Esterification; STEPHEN Aldehyde Synthesis; STEPHENS–CASTRO Acetylene Coupling; STETTER 1,4-Dicarbonyl Synthesis; STEVENS Ammonium Ylide Rearrangement; STIEGLITZ N -Haloamine Rearrangement; STILES–SISTI Grignard Formylation; STILLE Carbonyl Synthesis; STILLE Cross Coupling; STILL–GENNARI Z-Olefin Synthesis; STOBBE Succinic Ester Condensation; STOLTZ Asymmetric Ketone α-Allylation; STORK–HUNIG Cyanohydrin Alkylation; STORK Enamine Alkylation; STORK Radical Cyclization; STORK Reductive Cyclization; STORK–HAUSER Aminonitrile Alkylation; STORK–ZHAO Z -Iodo-olefin Synthesis; STORY Macrocycle Synthesis; STRECKER Aminoacid Synthesis; STRYKER Regioselective Reduction; SUAREZ Photochemical lodo Functionalization; SUZUKI Aromatic Nitration; SUZUKI Selective Nitrile Reduction; SUZUKI–MIYAURA C C Coupling; SWARTS Fluoroalkane Synthesis; SWERN Alcohol Oxidation; SZARVASY–SCHOPF Carbomethoxylation
James Mcnulty - One of the best experts on this subject based on the ideXlab platform.
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A convenient total synthesis of sphingosine-1-phosphate sphingosyl triazoles and their truncated analogs
2007Co-Authors: Zaheer Ahmed, James McnultyAbstract:A convenient total synthesis of D-erythro-sphingosine-1-phosphate and its truncated C-10 analog starting from D-galactose is described. Key steps included a Staudinger Azide Reduction and a highly chemoselective benzylidene hydrolysis in the presence of an N-Boc group. We also reported a convenient isolation protocol involving the direct precipitation and crystallization of sphingosine-1phosphate and its truncated C-10 analog. The application of this strategy provides sphingosyl triazoles and their analogs as major products and in good yield.