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Homologation of the Fischer Indolization: A Quinoline Synthesis via Homo-Diaza-Cope Rearrangement.

ABSTRACT: We disclose a new Brønsted acid promoted quinoline synthesis, proceeding via homo-diaza-Cope rearrangement of N-aryl-N'-cyclopropyl hydrazines. Our strategy can be considered a homologation of Fischer's classical indole synthesis and delivers 6-membered N-heterocycles, including previously inaccessible pyridine derivatives. This approach can also be used as a pyridannulation methodology toward constructing polycyclic polyheteroaromatics. A computational analysis has been employed to probe plausible activation modes and to interrogate the role of the catalyst.

SUBMITTER: Gerosa GG

PROVIDER: S-EPMC7693176 | biostudies-literature | 2020 Nov

REPOSITORIES: biostudies-literature

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Homologation of the Fischer Indolization: A Quinoline Synthesis via Homo-Diaza-Cope Rearrangement.

Gerosa Gabriela Guillermina GG Schwengers Sebastian Armin SA Maji Rajat R De Chandra Kanta CK List Benjamin B

Angewandte Chemie (International ed. in English) 20200907 46

We disclose a new Brønsted acid promoted quinoline synthesis, proceeding via homo-diaza-Cope rearrangement of N-aryl-N'-cyclopropyl hydrazines. Our strategy can be considered a homologation of Fischer's classical indole synthesis and delivers 6-membered N-heterocycles, including previously inaccessible pyridine derivatives. This approach can also be used as a pyridannulation methodology toward constructing polycyclic polyheteroaromatics. A computational analysis has been employed to probe plausi ...[more]

PMID: 32621795

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