Intramolecular cyclization of enaminones involving arylpalladium complexes. Synthesis of carbazoles

Iida, Hideo; Yuasa, Yoko; Kibayashi, Chihiro

doi:10.1021/jo01303a003

Cited by 146 publications

(45 citation statements)

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“…Kibayashi and co-workers (8) reported the cyclization of enaminone 30, using palladium(I1) acetate, leading to dihydrocyclopenta[b]indole 31 in modest yield (24%).…”

Section: Preparation Of Tricyclic Compounds With Modijied C Ringmentioning

confidence: 99%

“…Enaminones, useful for our study, must be prepared in two steps, according to standard procedures recently described (8,9): condensation of 2-methyl-l,3-cyclohexanedione with substituted anilines followed by N-alkylation of the secondary enaminones thus obtained. Indeed, as we reported elsewhere (4), condensation between N-methylanilines and 2-methyl-1,3-cyclohexanedione failed, and secondary enaminones such as 10 are not photoreactive.…”

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confidence: 99%

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Photocyclization of aryl enaminones. An efficient route to indole alkaloid synthons

Gardette¹,

Gramain²,

Lepage³

et al. 1989

Can. J. Chem.

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Chem. 67, 213 (1989).The photocyclization of enaminones was extended to aryl enaminones bearing a substituent on the aromatic moiety. This reaction was studied in order to achieve the synthesis of indole alkaloid synthons. Trials of regioselectivity control were made by using groups with enhanced steric hindrance. The reactivity of secondary enaminones was tested, and the ratio of C-alkylation to N-alkylation was shown to be dependent on the nature of the aromatic substituent. During this work, new hexahydrocarbazolones were synthesized, with substituents on the A ring or the modified C ring. Chem. 67,213 (1989).La photocyclisation d'knaminones a Ct C gCnCralisCe aux aryl-Cnaminones substituees sur la partie aromatique. Cette reaction a Ct C CtudiCe afin de synthitiser des prCcurseurs d'alcaloi'des indoliques. Des essais de contr8le de rCgiosClectivitC ont Ct C effectuCs en utilisant des groupements d'encombrement diffCrcnt. La rCactivite des Cnaminones secondaires a Ct C testCe et nous avons montrC l'influence de la nature du substituant aromatique sur le rapport C-alkylation, N-alkylation. Au cours de ce travail, de nouvelles hexahydrocarbazolones ont Ct C synthttistes avec des substituants sur le cycle A ou sur le cycle C-modifi6.

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“…Kibayashi and co-workers (8) reported the cyclization of enaminone 30, using palladium(I1) acetate, leading to dihydrocyclopenta[b]indole 31 in modest yield (24%).…”

Section: Preparation Of Tricyclic Compounds With Modijied C Ringmentioning

confidence: 99%

mentioning

confidence: 99%

Photocyclization of aryl enaminones. An efficient route to indole alkaloid synthons

Gardette¹,

Gramain²,

Lepage³

et al. 1989

Can. J. Chem.

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“…Over the last century, the synthesis of indoles has been an important area of research for organic chemists, and several powerful methods for the synthesis of indoles have been reported. [6] However, lack of starting material availability and functional-group tolerance often limits the generalization of a particular indole synthesis method. The development of mild, selective, and efficient methods for the synthesis of such compounds is highly desirable.…”

Section: Introductionmentioning

confidence: 99%

Exploring the Oxidative Cyclization of Substituted N‐Aryl Enamines: Pd‐Catalyzed Formation of Indoles from Anilines

Neumann

Rakshit

Dröge

et al. 2011

Chemistry A European J

175

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The direct Pd-catalyzed oxidative coupling of two C-H-bonds within N-aryl-enamines 1 allows the efficient formation of differently substituted indoles 2. In this cross-dehydrogenative coupling, many different functional groups are tolerated and the starting material N-aryl-enamines 1 can be easily prepared in one step from commercially available anilines. In addition, the whole sequence can also be run in a one-pot fashion. Optimization data, mechanistic insight, substrate scope, and applications are reported in this full paper.

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“…In this synthesis a palladium-catalysed intramolecular Heck-reaction was used to build the tricyclic indole core in a short and concise sequence (Scheme 26) [35–36]. …”

Section: Reviewmentioning

confidence: 99%

An overview of the key routes to the best selling 5-membered ring heterocyclic pharmaceuticals

Baumann¹,

Baxendale²,

Ley³

et al. 2011

Beilstein J. Org. Chem.

497

269

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SummaryThis review presents a comprehensive overview on selected synthetic routes towards commercial drug compounds as published in both journal and patent literature. Owing to the vast number of potential structures, we have concentrated only on those drugs containing five-membered heterocycles and focused principally on the assembly of the heterocyclic core. In order to target the most representative chemical entities the examples discussed have been selected from the top 200 best selling drugs of recent years.

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Intramolecular cyclization of enaminones involving arylpalladium complexes. Synthesis of carbazoles

Cited by 146 publications

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Photocyclization of aryl enaminones. An efficient route to indole alkaloid synthons

Photocyclization of aryl enaminones. An efficient route to indole alkaloid synthons

Exploring the Oxidative Cyclization of Substituted N‐Aryl Enamines: Pd‐Catalyzed Formation of Indoles from Anilines

An overview of the key routes to the best selling 5-membered ring heterocyclic pharmaceuticals

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