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The Cadogan–Sundberg indole synthesis, or simply Cadogan indole synthesis, is a name reaction in organic chemistry that allows for the generation of indoles from o-nitrostyrenes with the use of trialkyl phosphites, such as triethyl phosphite.[1][2][3][4][5][6][7]
Mechanism
o-nitrostyrene first reacts with triethyl phosphite, and the nitro group is converted to a nitroso group. The nitroso group then reacts with the alkene, and N-hydroxylindole is formed, which reacts again with triethyl phosphite to form the indole.[1][2][3][4]
Application
The Cadogan–Sundberg indole synthesis has been used as an intermediate step in the total synthesis of Tjipanazole E,[8] transforming 2-[trans-2-[5-Chloro-2-nitrophenyl)vinyl]-5-chloro-1H-indole to 5,5’-Dichloro-2,2’-biindole.
References
Cadogan, John Ivan George; Mackie, R. K. (1974). "Tervalent phosphorus compounds in organic synthesis". Chemical Society Reviews. 3 (1): 87–137. doi:10.1039/CS9740300087.
Wang, Zerong (15 September 2010). Comprehensive Organic Name Reactions and Reagents. doi:10.1002/9780470638859.conrr128. ISBN 9780470638859.
Sundberg, Richard J.; Yamazaki, Toshio (1 February 1967). "Rearrangements and ring expansions during the deoxygenation of β,β-disubstituted o-nitrostyrenes". The Journal of Organic Chemistry. 32 (2): 290–294. doi:10.1021/jo01288a009.
Sundberg, Richard J. (1 November 1965). "Deoxygenation of Nitro Groups by Trivalent Phosphorus. Indoles from o-Nitrostyrenes". The Journal of Organic Chemistry. 30 (11): 3604–3610. doi:10.1021/jo01022a006.
Gribble, Gordon W. (17 June 2016). "Cadogan–Sundberg Indole Synthesis". Indole Ring Synthesis: From Natural Products to Drug Discovery. pp. 266–277. doi:10.1002/9781118695692.ch26. ISBN 9781118695692.
Majgier-Baranowska, Helena; Williams, John D.; Li, Bing; Peet, Norton P. (1 February 1967). "Studies on the mechanism of the Cadogan–Sundberg indole synthesis". Tetrahedron Letters. 53 (35): 4785–4788. doi:10.1016/j.tetlet.2012.06.146.
Li, Jie Jack (4 January 2014). "Cadogan–Sundberg indole synthesis". Indole Ring Synthesis: From Natural Products to Drug Discovery. Springer. p. 102-103. doi:10.1007/978-3-319-03979-4_49. ISBN 978-3-319-03979-4.
Kuethe, Jeffrey T.; Wong, Audrey; Davies, Iaan W. (3 September 2003). "Effective Strategy for the Preparation of Indolocarbazole Aglycons and Glycosides: Total Synthesis of Tjipanazoles B, D, E, and I". Organic Letters. 5 (20): 3721–3723. doi:10.1021/ol035418r. PMID 14507214.
Topics in organic reactions
Addition reaction Elimination reaction Polymerization Reagents Rearrangement reaction Redox reaction Regioselectivity Stereoselectivity Stereospecificity Substitution reaction
A value Alpha effect Annulene Anomeric effect Antiaromaticity Aromatic ring current Aromaticity Baird's rule Baker–Nathan effect Baldwin's rules Bema Hapothle Beta-silicon effect Bicycloaromaticity Bredt's rule Bürgi–Dunitz angle Catalytic resonance theory Charge remote fragmentation Charge-transfer complex Clar's rule Conformational isomerism Conjugated system Conrotatory and disrotatory Curtin–Hammett principle Dynamic binding (chemistry) Edwards equation Effective molarity Electromeric effect Electron-rich Electron-withdrawing group Electronic effect Electrophile Evelyn effect Flippin–Lodge angle Free-energy relationship Grunwald–Winstein equation Hammett acidity function Hammett equation George S. Hammond Hammond's postulate Homoaromaticity Hückel's rule Hyperconjugation Inductive effect Kinetic isotope effect LFER solvent coefficients (data page) Marcus theory Markovnikov's rule Möbius aromaticity Möbius–Hückel concept More O'Ferrall–Jencks plot Negative hyperconjugation Neighbouring group participation 2-Norbornyl cation Nucleophile Kennedy J. P. Orton Passive binding Phosphaethynolate Polar effect Polyfluorene Ring strain Σ-aromaticity Spherical aromaticity Spiroaromaticity Steric effects Superaromaticity Swain–Lupton equation Taft equation Thorpe–Ingold effect Vinylogy Walsh diagram Woodward–Hoffmann rules Woodward's rules Y-aromaticity Yukawa–Tsuno equation Zaitsev's rule Σ-bishomoaromaticity
List of organic reactions
Carbon-carbon
bond forming
reactions
Acetoacetic ester synthesis Acyloin condensation Aldol condensation Aldol reaction Alkane metathesis Alkyne metathesis Alkyne trimerisation Alkynylation Allan–Robinson reaction Arndt–Eistert reaction Auwers synthesis Aza-Baylis–Hillman reaction Barbier reaction Barton–Kellogg reaction Baylis–Hillman reaction Benary reaction Bergman cyclization Biginelli reaction Bingel reaction Blaise ketone synthesis Blaise reaction Blanc chloromethylation Bodroux–Chichibabin aldehyde synthesis Bouveault aldehyde synthesis Bucherer–Bergs reaction Buchner ring expansion Cadiot–Chodkiewicz coupling Carbonyl allylation Carbonyl olefin metathesis Castro–Stephens coupling Chan rearrangement Chan–Lam coupling Claisen condensation Claisen rearrangement Claisen-Schmidt condensation Combes quinoline synthesis Corey–Fuchs reaction Corey–House synthesis Coupling reaction Cross-coupling reaction Cross dehydrogenative coupling Cross-coupling partner Dakin–West reaction Darzens reaction Diels–Alder reaction Doebner reaction Wulff–Dötz reaction Ene reaction Enyne metathesis Ethenolysis Favorskii reaction Ferrier carbocyclization Friedel–Crafts reaction Fujimoto–Belleau reaction Fujiwara–Moritani reaction Fukuyama coupling Gabriel–Colman rearrangement Gattermann reaction Glaser coupling Grignard reaction Grignard reagent Hammick reaction Heck reaction Henry reaction Heterogeneous metal catalyzed cross-coupling High dilution principle Hiyama coupling Homologation reaction Horner–Wadsworth–Emmons reaction Hydrocyanation Hydrovinylation Hydroxymethylation Ivanov reaction Johnson–Corey–Chaykovsky reaction Julia olefination Julia–Kocienski olefination Kauffmann olefination Knoevenagel condensation Knorr pyrrole synthesis Kolbe–Schmitt reaction Kowalski ester homologation Kulinkovich reaction Kumada coupling Liebeskind–Srogl coupling Malonic ester synthesis Mannich reaction McMurry reaction Meerwein arylation Methylenation Michael reaction Minisci reaction Mizoroki-Heck vs. Reductive Heck Nef isocyanide reaction Nef synthesis Negishi coupling Nierenstein reaction Nitro-Mannich reaction Nozaki–Hiyama–Kishi reaction Olefin conversion technology Olefin metathesis Palladium–NHC complex Passerini reaction Peterson olefination Pfitzinger reaction Piancatelli rearrangement Pinacol coupling reaction Prins reaction Quelet reaction Ramberg–Bäcklund reaction Rauhut–Currier reaction Reformatsky reaction Reimer–Tiemann reaction Rieche formylation Ring-closing metathesis Robinson annulation Sakurai reaction Seyferth–Gilbert homologation Shapiro reaction Sonogashira coupling Stetter reaction Stille reaction Stollé synthesis Stork enamine alkylation Suzuki reaction Takai olefination Thermal rearrangement of aromatic hydrocarbons Thorpe reaction Ugi reaction Ullmann reaction Wagner-Jauregg reaction Weinreb ketone synthesis Wittig reaction Wurtz reaction Wurtz–Fittig reaction Zincke–Suhl reaction
Homologation reactions
Arndt–Eistert reaction Hooker reaction Kiliani–Fischer synthesis Kowalski ester homologation Methoxymethylenetriphenylphosphorane Seyferth–Gilbert homologation Wittig reaction
Olefination reactions
Bamford–Stevens reaction Barton–Kellogg reaction Boord olefin synthesis Chugaev elimination Cope reaction Corey–Winter olefin synthesis Dehydrohalogenation Elimination reaction Grieco elimination Hofmann elimination Horner–Wadsworth–Emmons reaction Hydrazone iodination Julia olefination Julia–Kocienski olefination Kauffmann olefination McMurry reaction Peterson olefination Ramberg–Bäcklund reaction Shapiro reaction Takai olefination Wittig reaction
Carbon-heteroatom
bond forming
reactions
Azo coupling Bartoli indole synthesis Boudouard reaction Cadogan–Sundberg indole synthesis Diazonium compound Esterification Grignard reagent Haloform reaction Hegedus indole synthesis Hurd–Mori 1,2,3-thiadiazole synthesis Kharasch–Sosnovsky reaction Knorr pyrrole synthesis Leimgruber–Batcho indole synthesis Mukaiyama hydration Nenitzescu indole synthesis Oxymercuration reaction Reed reaction Schotten–Baumann reaction Ullmann condensation Williamson ether synthesis Yamaguchi esterification
Degradation
reactions
Barbier–Wieland degradation Bergmann degradation Edman degradation Emde degradation Gallagher–Hollander degradation Hofmann rearrangement Hooker reaction Isosaccharinic acid Marker degradation Ruff degradation Strecker degradation Von Braun amide degradation Weerman degradation Wohl degradation
Organic redox
reactions
Acyloin condensation Adkins–Peterson reaction Akabori amino-acid reaction Alcohol oxidation Algar–Flynn–Oyamada reaction Amide reduction Andrussow process Angeli–Rimini reaction Aromatization Autoxidation Baeyer–Villiger oxidation Barton–McCombie deoxygenation Bechamp reduction Benkeser reaction Bergmann degradation Birch reduction Bohn–Schmidt reaction Bosch reaction Bouveault–Blanc reduction Boyland–Sims oxidation Cannizzaro reaction Carbonyl reduction Clemmensen reduction Collins oxidation Corey–Itsuno reduction Corey–Kim oxidation Corey–Winter olefin synthesis Criegee oxidation Dakin oxidation Davis oxidation Deoxygenation Dess–Martin oxidation DNA oxidation Elbs persulfate oxidation Emde degradation Eschweiler–Clarke reaction Étard reaction Fischer–Tropsch process Fleming–Tamao oxidation Fukuyama reduction Ganem oxidation Glycol cleavage Griesbaum coozonolysis Grundmann aldehyde synthesis Haloform reaction Hydrogenation Hydrogenolysis Hydroxylation Jones oxidation Kiliani–Fischer synthesis Kolbe electrolysis Kornblum oxidation Kornblum–DeLaMare rearrangement Leuckart reaction Ley oxidation Lindgren oxidation Lipid peroxidation Lombardo methylenation Luche reduction Markó–Lam deoxygenation McFadyen–Stevens reaction Meerwein–Ponndorf–Verley reduction Methionine sulfoxide Miyaura borylation Mozingo reduction Noyori asymmetric hydrogenation Omega oxidation Oppenauer oxidation Oxygen rebound mechanism Ozonolysis Parikh–Doering oxidation Pinnick oxidation Prévost reaction Reduction of nitro compounds Reductive amination Riley oxidation Rosenmund reduction Rubottom oxidation Sabatier reaction Sarett oxidation Selenoxide elimination Shapiro reaction Sharpless asymmetric dihydroxylation Epoxidation of allylic alcohols Sharpless epoxidation Sharpless oxyamination Stahl oxidation Staudinger reaction Stephen aldehyde synthesis Swern oxidation Transfer hydrogenation Wacker process Wharton reaction Whiting reaction Wohl–Aue reaction Wolff–Kishner reduction Wolffenstein–Böters reaction Zinin reaction
Rearrangement
reactions
1,2-rearrangement 1,2-Wittig rearrangement 2,3-sigmatropic rearrangement 2,3-Wittig rearrangement Achmatowicz reaction Alkyne zipper reaction Allen–Millar–Trippett rearrangement Allylic rearrangement Alpha-ketol rearrangement Amadori rearrangement Arndt–Eistert reaction Aza-Cope rearrangement Baker–Venkataraman rearrangement Bamberger rearrangement Banert cascade Beckmann rearrangement Benzilic acid rearrangement Bergman cyclization Bergmann degradation Boekelheide reaction Brook rearrangement Buchner ring expansion Carroll rearrangement Chan rearrangement Claisen rearrangement Cope rearrangement Corey–Fuchs reaction Cornforth rearrangement Criegee rearrangement Curtius rearrangement Demjanov rearrangement Di-π-methane rearrangement Dimroth rearrangement Divinylcyclopropane-cycloheptadiene rearrangement Dowd–Beckwith ring-expansion reaction Electrocyclic reaction Ene reaction Enyne metathesis Favorskii reaction Favorskii rearrangement Ferrier carbocyclization Ferrier rearrangement Fischer–Hepp rearrangement Fries rearrangement Fritsch–Buttenberg–Wiechell rearrangement Gabriel–Colman rearrangement Group transfer reaction Halogen dance rearrangement Hayashi rearrangement Hofmann rearrangement Hofmann–Martius rearrangement Ireland–Claisen rearrangement Jacobsen rearrangement Kornblum–DeLaMare rearrangement Kowalski ester homologation Lobry de Bruyn–Van Ekenstein transformation Lossen rearrangement McFadyen–Stevens reaction McLafferty rearrangement Meyer–Schuster rearrangement Mislow–Evans rearrangement Mumm rearrangement Myers allene synthesis Nazarov cyclization reaction Neber rearrangement Newman–Kwart rearrangement Overman rearrangement Oxy-Cope rearrangement Pericyclic reaction Piancatelli rearrangement Pinacol rearrangement Pummerer rearrangement Ramberg–Bäcklund reaction Ring expansion and contraction Ring-closing metathesis Rupe reaction Schmidt reaction Semipinacol rearrangement Seyferth–Gilbert homologation Sigmatropic reaction Skattebøl rearrangement Smiles rearrangement Sommelet–Hauser rearrangement Stevens rearrangement Stieglitz rearrangement Thermal rearrangement of aromatic hydrocarbons Tiffeneau–Demjanov rearrangement Vinylcyclopropane rearrangement Wagner–Meerwein rearrangement Wallach rearrangement Weerman degradation Westphalen–Lettré rearrangement Willgerodt rearrangement Wolff rearrangement
Ring forming
reactions
1,3-Dipolar cycloaddition Annulation Azide-alkyne Huisgen cycloaddition Baeyer–Emmerling indole synthesis Bartoli indole synthesis Bergman cyclization Biginelli reaction Bischler–Möhlau indole synthesis Bischler–Napieralski reaction Blum–Ittah aziridine synthesis Bobbitt reaction Bohlmann–Rahtz pyridine synthesis Borsche–Drechsel cyclization Bucherer carbazole synthesis Bucherer–Bergs reaction Cadogan–Sundberg indole synthesis Camps quinoline synthesis Chichibabin pyridine synthesis Cook–Heilbron thiazole synthesis Cycloaddition Darzens reaction Davis–Beirut reaction De Kimpe aziridine synthesis Debus–Radziszewski imidazole synthesis Dieckmann condensation Diels–Alder reaction Feist–Benary synthesis Ferrario–Ackermann reaction Fiesselmann thiophene synthesis Fischer indole synthesis Fischer oxazole synthesis Friedländer synthesis Gewald reaction Graham reaction Hantzsch pyridine synthesis Hegedus indole synthesis Hemetsberger indole synthesis Hofmann–Löffler reaction Hurd–Mori 1,2,3-thiadiazole synthesis Iodolactonization Isay reaction Jacobsen epoxidation Johnson–Corey–Chaykovsky reaction Knorr pyrrole synthesis Knorr quinoline synthesis Kröhnke pyridine synthesis Kulinkovich reaction Larock indole synthesis Madelung synthesis Nazarov cyclization reaction Nenitzescu indole synthesis Niementowski quinazoline synthesis Niementowski quinoline synthesis Paal–Knorr synthesis Paternò–Büchi reaction Pechmann condensation Petrenko-Kritschenko piperidone synthesis Pictet–Spengler reaction Pomeranz–Fritsch reaction Prilezhaev reaction Pschorr cyclization Reissert indole synthesis Ring-closing metathesis Robinson annulation Sharpless epoxidation Simmons–Smith reaction Skraup reaction Urech hydantoin synthesis Van Leusen reaction Wenker synthesis
Cycloaddition
1,3-Dipolar cycloaddition 4+4 Photocycloaddition (4+3) cycloaddition 6+4 Cycloaddition Alkyne trimerisation Aza-Diels–Alder reaction Azide-alkyne Huisgen cycloaddition Bradsher cycloaddition Cheletropic reaction Conia-ene reaction Cyclopropanation Diazoalkane 1,3-dipolar cycloaddition Diels–Alder reaction Enone–alkene cycloadditions Hexadehydro Diels–Alder reaction Imine Diels–Alder reaction Intramolecular Diels–Alder cycloaddition Inverse electron-demand Diels–Alder reaction Ketene cycloaddition McCormack reaction Metal-centered cycloaddition reactions Nitrone-olefin (3+2) cycloaddition Oxo-Diels–Alder reaction Ozonolysis Pauson–Khand reaction Povarov reaction Prato reaction Retro-Diels–Alder reaction Staudinger synthesis Trimethylenemethane cycloaddition Vinylcyclopropane (5+2) cycloaddition Wagner-Jauregg reaction
Heterocycle forming reactions
Algar–Flynn–Oyamada reaction Allan–Robinson reaction Auwers synthesis Bamberger triazine synthesis Banert cascade Barton–Zard reaction Bernthsen acridine synthesis Bischler–Napieralski reaction Bobbitt reaction Boger pyridine synthesis Borsche–Drechsel cyclization Bucherer carbazole synthesis Bucherer–Bergs reaction Chichibabin pyridine synthesis Cook–Heilbron thiazole synthesis Diazoalkane 1,3-dipolar cycloaddition Einhorn–Brunner reaction Erlenmeyer–Plöchl azlactone and amino-acid synthesis Feist–Benary synthesis Fischer oxazole synthesis Gabriel–Colman rearrangement Gewald reaction Hantzsch ester Hantzsch pyridine synthesis Herz reaction Knorr pyrrole synthesis Kröhnke pyridine synthesis Lectka enantioselective beta-lactam synthesis Lehmstedt–Tanasescu reaction Niementowski quinazoline synthesis Nitrone-olefin (3+2) cycloaddition Paal–Knorr synthesis Pellizzari reaction Pictet–Spengler reaction Pomeranz–Fritsch reaction Prilezhaev reaction Robinson–Gabriel synthesis Stollé synthesis Urech hydantoin synthesis Wenker synthesis Wohl–Aue reaction
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