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Jie Jack Li - One of the best experts on this subject based on the ideXlab platform.

  • Pomeranz-Fritsch Reaction
    2020
    Co-Authors: Jie Jack Li
    Abstract:

    Isoquinoline and saturated variants synthesis via acid-mediated cyclization of the appropriate aminoacetal intermediate.

  • Name Reactions A Collection of Detailed Mechanisms and Synthetic Applications
    2020
    Co-Authors: Jie Jack Li
    Abstract:

    Alder ene Reaction -- Aldol condensation -- Algar-Flynn-Oyamada Reaction -- Allan-Robinson Reaction -- Appel Reaction -- Arndt-Eistert homologation -- Baeyer-Villiger oxidation -- Baker-Venkataraman rearrangement -- Bamberger rearrangement -- Bamford-Stevens Reaction -- Barbier coupling Reaction -- Bargellini Reaction -- Bartoli indole synthesis -- Barton radical decarboxylation -- Barton-McCombie deoxygenation -- Barton nitrite photolysis -- Barton-Zard Reaction -- Batcho-Leimgruber indole synthesis -- Baylis-Hillman Reaction -- Beckmann rearrangement -- Beirut Reaction -- Benzilic acid rearrangement -- Benzoin condensation -- Bergman cyclization -- Biginelli pyrimidone synthesis -- Birch reduction -- Bischler-Mohlau indole synthesis -- Bischler-Napieralski Reaction -- Blaise Reaction -- Blanc chloromethylation -- Blum aziridine synthesis -- Boekelheide Reaction -- Boger pyridine synthesis -- Borch reductive amination -- Borsche-Drechsel cyclization -- Boulton-Katritzky rearrangement -- Bouveault aldehyde synthesis -- Bouveault-Blanc reduction -- Boyland-Sims oxidation -- Bradsher Reaction -- Brook rearrangement -- Brown hydroboration -- Bucherer carbazole synthesis -- Bucherer Reaction -- Bucherer-Bergs Reaction -- Buchner-Curtius-Schlotterbeck Reaction -- Buchner method of ring expansion -- Buchwald-Hartwig C-N and C-O bond formation Reactions -- Burgess dehydrating reagent -- Cadiot-Chodkiewicz coupling -- Camps quinolinol synthesis -- Cannizzaro disproportionation -- Carroll rearrangement -- Castro-Stephens coupling -- Chan alkyne reduction -- Chan-Lam coupling Reaction -- Chapman rearrangement -- Chichibabin pyridine synthesis -- Chugaev elimination -- Ciamician-Dennsted rearrangement -- Claisen condensation -- Claisen isoxazole synthesis -- Claisen rearrangements -- Clemmensen reduction -- Combes quinoline synthesis -- Conrad-Limpach Reaction -- Cope elimination Reaction -- Cope rearrangement -- Corey-Bakshi-Shibata (CBS) reduction -- Corey-Chaykovsky Reaction -- Corey-Fuchs Reaction -- Corey-Kim oxidation -- Corey-Nicolaou macrolactonization -- Corey-Seebach Reaction -- Corey-Winter olefin synthesis -- Criegee glycol cleavage -- Criegee mechanism of ozonolysis -- Curtius rearrangement -- Dakin oxidation -- Dakin-West Reaction -- Danheiser annulation -- Darzens glycidic ester condensation -- Davis chiral oxaziridine reagents -- Delepine amine synthesis -- de Mayo Reaction -- Demjanov rearrangement -- Dess-Martin periodinane oxidation -- Dieckmann condensation -- Diels-Alder Reaction -- Dienone-phenol rearrangement -- Di-?-methane rearrangement -- Doebner quinoline synthesis -- Dotz Reaction -- Dowd-Beckwith ring expansion -- Erlenmeyer-Plochl azlactone synthesis -- Eschenmoser-Tanabe fragmentation -- Eschweiler-Clarke reductive alkylation of amines -- Evans aldol Reaction -- Favorskii rearrangement and quasi-Favorskii rearrangement -- Feist-Benary furan synthesis -- Ferrier carbocyclization -- Ferrier glycal allylic rearrangement -- Fiesselmann thiophene synthesis -- Fischer indole synthesis -- Fischer oxazole synthesis -- Fleming-Kumada oxidation -- Friedel-Crafts Reaction -- Friedlander quinoline synthesis -- Fries rearrangement -- Fukuyama amine synthesis -- Fukuyama reduction -- Gabriel synthesis -- Gabriel-Colman rearrangement -- Gassman indole synthesis -- Gattermann-Koch Reaction -- Gewald aminothiophene synthesis -- Glaser coupling -- Gomberg-Bachmann Reaction -- Gould-Jacobs Reaction -- Grignard Reaction -- Grob fragmentation -- Guareschi-Thorpe condensation -- Hajos-Wiechert Reaction -- Haller-Bauer Reaction -- Hantzsch dihydropyridine synthesis -- Hantzsch pyrrole synthesis -- Heck Reaction -- Hegedus indole synthesis -- Hell-Volhard-Zelinsky Reaction -- Henry nitroaldol Reaction -- Hinsberg synthesis of thiophene derivatives -- Hiyama cross-coupling Reaction -- Hofmann rearrangement -- Hofmann-Loffler-Freytag Reaction -- Horner-Wadsworth-Emmons Reaction -- Houben-Hoesch Reaction -- Hunsdiecker-Borodin Reaction -- Hurd-Mori 1,2,3-thiadiazole synthesis -- Jacobsen-Katsuki epoxidation -- Japp-Klingemann hydrazone synthesis -- Jones oxidation -- Julia-Kocienski olefination -- Julia-Lythgoe olefination -- Kahne-Crich glycosidation -- Keck macrolactonization -- Knoevenagel condensation -- Knorr pyrazole synthesis -- Koch-Haaf carbonylation -- Koenig-Knorr glycosidation -- Kolbe-Schmitt Reaction -- Kostanecki Reaction -- Krohnke pyridine synthesis -- Kumada cross-coupling Reaction -- Lawesson’s reagent -- Leuckart-Wallach Reaction -- Lossen rearrangement -- McFadyen-Stevens reduction -- McMurry coupling -- MacMillan catalyst -- Mannich Reaction -- Marshall boronate fragmentation -- Martin’s sulfurane dehydrating reagent -- Masamune-Roush conditions -- Meerwein-Ponndorf-Verley reduction -- Meisenheimer complex -- [1,2]-Meisenheimer rearrangement -- [2,3]-Meisenheimer rearrangement -- Meth-Cohn quinoline synthesis -- Meyers oxazoline method -- Meyer-Schuster rearrangement -- Michael addition -- Michaelis-Arbuzov phosphonate synthesis -- Midland reduction -- Mislow-Evans rearrangement -- Mitsunobu Reaction -- Miyaura borylation -- Moffatt oxidation -- Montgomery coupling -- Morgan-Walls Reaction -- Mori-Ban indole synthesis -- Mukaiyama aldol Reaction -- Mukaiyama Michael addition -- Mukaiyama reagent -- Myers-Saito cyclization -- Nazarov cyclization -- Neber rearrangement -- Nef Reaction -- Negishi cross-coupling Reaction -- Nenitzescu indole synthesis -- Nicholas Reaction -- Nicolaou dehydrogenation -- Nicolaou hydroxy-dithioketal cyclization -- Nicolaou hydroxy-ketone reductive cyclic ether formation -- Nicolaou oxyselenation -- Noyori asymmetric hydrogenation -- Nozaki-Hiyama-Kishi Reaction -- Oppenauer oxidation -- Overman rearrangement -- Paal thiophene synthesis -- Paal-Knorr furan synthesis -- Parham cyclization -- Passerini Reaction -- Paterno-Buchi Reaction -- Pauson-Khand cyclopentenone synthesis -- Payne rearrangement -- Pechmann coumarin synthesis -- Perkin Reaction -- Petasis Reaction -- Peterson olefination -- Pictet-Gams isoquinoline synthesis -- Pictet-Spengler tetrahydroisoquinoline synthesis -- Pinacol rearrangement -- Pinner Reaction -- Polonovski Reaction -- Polonovski-Potier Reaction -- Pomeranz-Fritsch Reaction -- Prevost trans-dihydroxylation -- Prins Reaction -- Pschorr cyclization -- Pummerer rearrangement -- Ramberg-Backlund Reaction -- Reformatsky Reaction -- Regitz diazo synthesis -- Reimer-Tiemann Reaction -- Reissert aldehyde synthesis -- Reissert indole synthesis -- Ring-closing metathesis (RCM) -- Ritter Reaction -- Robinson annulation -- Robinson-Gabriel synthesis -- Robinson-Schopf Reaction -- Rosenmund reduction -- Rubottom oxidation -- Rupe rearrangement -- Saegusa oxidation -- Sakurai allylation Reaction -- Sandmeyer Reaction -- Schiemann Reaction -- Schmidt Reaction -- Schmidt’s trichloroacetimidate glycosidation Reaction -- Shapiro Reaction -- Sharpless asymmetric amino hydroxylation -- Sharpless asymmetric epoxidation -- Sharpless asymmetric dihydroxylation -- Sharpless olefin synthesis -- Simmons-Smith Reaction -- Skraup quinoline synthesis -- Smiles rearrangement -- Sommelet Reaction -- Sommelet-Hauser rearrangement -- Sonogashira Reaction -- Staudinger ketene cycloaddition -- Staudinger reduction -- Sternbach benzodiazepine synthesis -- Stetter Reaction -- Still-Gennari phosphonate Reaction -- Stille coupling -- Stille-Kelly Reaction -- Stobbe condensation -- Stork enamine Reaction -- Strecker amino acid synthesis -- Suzuki coupling -- Swern oxidation -- Takai iodoalkene synthesis -- Tebbe olefination -- TEMPO-mediated oxidation -- Thorpe-Ziegler Reaction -- Tsuji-Trost Reaction -- Ugi Reaction -- Ullmann Reaction -- van Leusen oxazole synthesis -- Vilsmeier-Haack Reaction -- Vilsmeier mechanism for acid chloride formation -- Vinylcyclopropane-cyclopentene rearrangement -- von Braun Reaction -- Wacker oxidation -- Wagner-Meerwein rearrangement -- Weiss-Cook Reaction -- Wharton oxygen transposition Reaction -- Willgerodt-Kindler Reaction -- Wittig Reaction -- [1,2]-Wittig rearrangement -- [2,3]-Wittig rearrangement -- Wohl-Ziegler Reaction -- Wolff rearrangement -- Wolff-Kishner reduction -- Yamaguchi esterification -- Zincke Reaction.

  • Name Reactions: A Collection of Detailed Reaction Mechanisms
    2002
    Co-Authors: Jie Jack Li
    Abstract:

    Alder ene Reaction -- Aldol condensation -- Algar-Flynn-Oyamada Reaction -- Allan-Robinson Reaction -- Appel Reaction -- Arndt-Eistert homologation -- Baeyer-Villiger oxidation -- Baker-Venkataraman rearrangement -- Bamberger rearrangement -- Bamford-Stevens Reaction -- Barbier coupling Reaction -- Bargellini Reaction -- Bartoli indole synthesis -- Barton radical decarboxylation -- Barton-McCombie deoxygenation -- Barton nitrite photolysis -- Barton-Zard Reaction -- Batcho-Leimgruber indole synthesis -- Baylis-Hillman Reaction -- Beckmann rearrangement -- Beirut Reaction -- Benzilic acid rearrangement -- Benzoin condensation -- Bergman cyclization -- Biginelli pyrimidone synthesis -- Birch reduction -- Bischler-Mohlau indole synthesis -- Bischler-Napieralski Reaction -- Blaise Reaction -- Blanc chloromethylation -- Blum aziridine synthesis -- Boekelheide Reaction -- Boger pyridine synthesis -- Borch reductive amination -- Borsche-Drechsel cyclization -- Boulton-Katritzky rearrangement -- Bouveault aldehyde synthesis -- Bouveault-Blanc reduction -- Boyland-Sims oxidation -- Bradsher Reaction -- Brook rearrangement -- Brown hydroboration -- Bucherer carbazole synthesis -- Bucherer Reaction -- Bucherer-Bergs Reaction -- Buchner-Curtius-Schlotterbeck Reaction -- Buchner method of ring expansion -- Buchwald-Hartwig C-N and C-O bond formation Reactions -- Burgess dehydrating reagent -- Cadiot-Chodkiewicz coupling -- Camps quinolinol synthesis -- Cannizzaro disproportionation -- Carroll rearrangement -- Castro-Stephens coupling -- Chan alkyne reduction -- Chan-Lam coupling Reaction -- Chapman rearrangement -- Chichibabin pyridine synthesis -- Chugaev elimination -- Ciamician-Dennsted rearrangement -- Claisen condensation -- Claisen isoxazole synthesis -- Claisen rearrangements -- Clemmensen reduction -- Combes quinoline synthesis -- Conrad-Limpach Reaction -- Cope elimination Reaction -- Cope rearrangement -- Corey-Bakshi-Shibata (CBS) reduction -- Corey-Chaykovsky Reaction -- Corey-Fuchs Reaction -- Corey-Kim oxidation -- Corey-Nicolaou macrolactonization -- Corey-Seebach Reaction -- Corey-Winter olefin synthesis -- Criegee glycol cleavage -- Criegee mechanism of ozonolysis -- Curtius rearrangement -- Dakin oxidation -- Dakin-West Reaction -- Danheiser annulation -- Darzens glycidic ester condensation -- Davis chiral oxaziridine reagents -- Delepine amine synthesis -- de Mayo Reaction -- Demjanov rearrangement -- Dess-Martin periodinane oxidation -- Dieckmann condensation -- Diels-Alder Reaction -- Dienone-phenol rearrangement -- Di-?-methane rearrangement -- Doebner quinoline synthesis -- Dotz Reaction -- Dowd-Beckwith ring expansion -- Erlenmeyer-Plochl azlactone synthesis -- Eschenmoser-Tanabe fragmentation -- Eschweiler-Clarke reductive alkylation of amines -- Evans aldol Reaction -- Favorskii rearrangement and quasi-Favorskii rearrangement -- Feist-Benary furan synthesis -- Ferrier carbocyclization -- Ferrier glycal allylic rearrangement -- Fiesselmann thiophene synthesis -- Fischer indole synthesis -- Fischer oxazole synthesis -- Fleming-Kumada oxidation -- Friedel-Crafts Reaction -- Friedlander quinoline synthesis -- Fries rearrangement -- Fukuyama amine synthesis -- Fukuyama reduction -- Gabriel synthesis -- Gabriel-Colman rearrangement -- Gassman indole synthesis -- Gattermann-Koch Reaction -- Gewald aminothiophene synthesis -- Glaser coupling -- Gomberg-Bachmann Reaction -- Gould-Jacobs Reaction -- Grignard Reaction -- Grob fragmentation -- Guareschi-Thorpe condensation -- Hajos-Wiechert Reaction -- Haller-Bauer Reaction -- Hantzsch dihydropyridine synthesis -- Hantzsch pyrrole synthesis -- Heck Reaction -- Hegedus indole synthesis -- Hell-Volhard-Zelinsky Reaction -- Henry nitroaldol Reaction -- Hinsberg synthesis of thiophene derivatives -- Hiyama cross-coupling Reaction -- Hofmann rearrangement -- Hofmann-Loffler-Freytag Reaction -- Horner-Wadsworth-Emmons Reaction -- Houben-Hoesch Reaction -- Hunsdiecker-Borodin Reaction -- Hurd-Mori 1,2,3-thiadiazole synthesis -- Jacobsen-Katsuki epoxidation -- Japp-Klingemann hydrazone synthesis -- Jones oxidation -- Julia-Kocienski olefination -- Julia-Lythgoe olefination -- Kahne-Crich glycosidation -- Keck macrolactonization -- Knoevenagel condensation -- Knorr pyrazole synthesis -- Koch-Haaf carbonylation -- Koenig-Knorr glycosidation -- Kolbe-Schmitt Reaction -- Kostanecki Reaction -- Krohnke pyridine synthesis -- Kumada cross-coupling Reaction -- Lawesson’s reagent -- Leuckart-Wallach Reaction -- Lossen rearrangement -- McFadyen-Stevens reduction -- McMurry coupling -- MacMillan catalyst -- Mannich Reaction -- Marshall boronate fragmentation -- Martin’s sulfurane dehydrating reagent -- Masamune-Roush conditions -- Meerwein-Ponndorf-Verley reduction -- Meisenheimer complex -- [1,2]-Meisenheimer rearrangement -- [2,3]-Meisenheimer rearrangement -- Meth-Cohn quinoline synthesis -- Meyers oxazoline method -- Meyer-Schuster rearrangement -- Michael addition -- Michaelis-Arbuzov phosphonate synthesis -- Midland reduction -- Mislow-Evans rearrangement -- Mitsunobu Reaction -- Miyaura borylation -- Moffatt oxidation -- Montgomery coupling -- Morgan-Walls Reaction -- Mori-Ban indole synthesis -- Mukaiyama aldol Reaction -- Mukaiyama Michael addition -- Mukaiyama reagent -- Myers-Saito cyclization -- Nazarov cyclization -- Neber rearrangement -- Nef Reaction -- Negishi cross-coupling Reaction -- Nenitzescu indole synthesis -- Nicholas Reaction -- Nicolaou dehydrogenation -- Nicolaou hydroxy-dithioketal cyclization -- Nicolaou hydroxy-ketone reductive cyclic ether formation -- Nicolaou oxyselenation -- Noyori asymmetric hydrogenation -- Nozaki-Hiyama-Kishi Reaction -- Oppenauer oxidation -- Overman rearrangement -- Paal thiophene synthesis -- Paal-Knorr furan synthesis -- Parham cyclization -- Passerini Reaction -- Paterno-Buchi Reaction -- Pauson-Khand cyclopentenone synthesis -- Payne rearrangement -- Pechmann coumarin synthesis -- Perkin Reaction -- Petasis Reaction -- Peterson olefination -- Pictet-Gams isoquinoline synthesis -- Pictet-Spengler tetrahydroisoquinoline synthesis -- Pinacol rearrangement -- Pinner Reaction -- Polonovski Reaction -- Polonovski-Potier Reaction -- Pomeranz-Fritsch Reaction -- Prevost trans-dihydroxylation -- Prins Reaction -- Pschorr cyclization -- Pummerer rearrangement -- Ramberg-Backlund Reaction -- Reformatsky Reaction -- Regitz diazo synthesis -- Reimer-Tiemann Reaction -- Reissert aldehyde synthesis -- Reissert indole synthesis -- Ring-closing metathesis (RCM) -- Ritter Reaction -- Robinson annulation -- Robinson-Gabriel synthesis -- Robinson-Schopf Reaction -- Rosenmund reduction -- Rubottom oxidation -- Rupe rearrangement -- Saegusa oxidation -- Sakurai allylation Reaction -- Sandmeyer Reaction -- Schiemann Reaction -- Schmidt Reaction -- Schmidt’s trichloroacetimidate glycosidation Reaction -- Shapiro Reaction -- Sharpless asymmetric amino hydroxylation -- Sharpless asymmetric epoxidation -- Sharpless asymmetric dihydroxylation -- Sharpless olefin synthesis -- Simmons-Smith Reaction -- Skraup quinoline synthesis -- Smiles rearrangement -- Sommelet Reaction -- Sommelet-Hauser rearrangement -- Sonogashira Reaction -- Staudinger ketene cycloaddition -- Staudinger reduction -- Sternbach benzodiazepine synthesis -- Stetter Reaction -- Still-Gennari phosphonate Reaction -- Stille coupling -- Stille-Kelly Reaction -- Stobbe condensation -- Stork enamine Reaction -- Strecker amino acid synthesis -- Suzuki coupling -- Swern oxidation -- Takai iodoalkene synthesis -- Tebbe olefination -- TEMPO-mediated oxidation -- Thorpe-Ziegler Reaction -- Tsuji-Trost Reaction -- Ugi Reaction -- Ullmann Reaction -- van Leusen oxazole synthesis -- Vilsmeier-Haack Reaction -- Vilsmeier mechanism for acid chloride formation -- Vinylcyclopropane-cyclopentene rearrangement -- von Braun Reaction -- Wacker oxidation -- Wagner-Meerwein rearrangement -- Weiss-Cook Reaction -- Wharton oxygen transposition Reaction -- Willgerodt-Kindler Reaction -- Wittig Reaction -- [1,2]-Wittig rearrangement -- [2,3]-Wittig rearrangement -- Wohl-Ziegler Reaction -- Wolff rearrangement -- Wolff-Kishner reduction -- Yamaguchi esterification -- Zincke Reaction.

Anthony G M Barrett - One of the best experts on this subject based on the ideXlab platform.

Walter J. Gensler - One of the best experts on this subject based on the ideXlab platform.

  • Organic Reactions - The Synthesis of Isoquinolines by the Pomeranz-Fritsch Reaction
    Organic Reactions, 2011
    Co-Authors: Walter J. Gensler
    Abstract:

    Acid-catalyzed cyclization of benzalaminoacetal results in the formation of the isoquinoline nucleus. This Reaction, first reported by Pomeranz and Fritsch, has been used in the synthesis of a variety of isoquinoline compounds. The process is carried out in two stages. In step one, a condensation leads to the benzalaminacetal. In step two, a ring closure leads to the isoquinoline. An alternative route involves the condensation of the corresponding benzylamine witth glyoxal semiacetal. The yield of isoquinoline products varies widely. The Pomeranz-Fritsch synthesis offers the possibility of preparing isoquinolines with the substituent groups in an orientation difficult to achieve with other methods. Keywords: Pomeranz-Fritsch Reaction; isoquinolines; cyclization; Schiff base; acetals; glyoxyl semiacetal; experimental procedures

Yong Wu - One of the best experts on this subject based on the ideXlab platform.

  • A Versatile Total Synthesis of 8‐Oxyberberine and Oxohomoberberines
    Chinese Journal of Chemistry, 2014
    Co-Authors: Yun He, Yang Zheng, Yong Wu
    Abstract:

    The total syntheses of 8-oxyberberine and oxohomoberberines were accomplished starting from commercially available 5-bromobenzo[d][1,3]dioxole, piperonal and sesamol in high total yield. The key steps involved a modified Pomeranz-Fritsch Reaction and the intramolecular Heck cyclization. This approach is short, convenient and suitable for the preparation of homoberberine analogues.

Edward R Walker - One of the best experts on this subject based on the ideXlab platform.