Understanding and Interrupting the Fischer Azaindolization Reaction

Bryan J. Simmons; Marie Hoffmann; Pier Alexandre Champagne; Elias Picazo; Katsuya Yamakawa; Lucas A. Morrill; K. N. Houk; Neil K. Garg

doi:10.1021/jacs.7b07518

Understanding and Interrupting the Fischer Azaindolization Reaction

Bryan J. Simmons, Marie Hoffmann, Pier Alexandre Champagne, Elias Picazo, Katsuya Yamakawa, Lucas A. Morrill, K. N. Houk, Neil K. Garg

Research output: Contribution to journal › Article › peer-review

23 Scopus citations

Abstract

Experimental and computational studies pertaining to the Fischer azaindolization reaction are reported. These studies explain why pyridylhydrazines are poorly reactive in Fischer indolization reactions, in addition to the origin of hydrazine substituent effects. Additionally, an interrupted variant of Fischer azaindolization methodology is disclosed, which provides a synthetic entryway into fused azaindoline scaffolds.

Original language	English (US)
Pages (from-to)	14833-14836
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	139
Issue number	42
DOIs	https://doi.org/10.1021/jacs.7b07518
State	Published - Oct 25 2017
Externally published	Yes

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/jacs.7b07518

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AU - Hoffmann, Marie

AU - Champagne, Pier Alexandre

AU - Picazo, Elias

AU - Yamakawa, Katsuya

AU - Morrill, Lucas A.

AU - Houk, K. N.

AU - Garg, Neil K.

PY - 2017/10/25

Y1 - 2017/10/25

N2 - Experimental and computational studies pertaining to the Fischer azaindolization reaction are reported. These studies explain why pyridylhydrazines are poorly reactive in Fischer indolization reactions, in addition to the origin of hydrazine substituent effects. Additionally, an interrupted variant of Fischer azaindolization methodology is disclosed, which provides a synthetic entryway into fused azaindoline scaffolds.

AB - Experimental and computational studies pertaining to the Fischer azaindolization reaction are reported. These studies explain why pyridylhydrazines are poorly reactive in Fischer indolization reactions, in addition to the origin of hydrazine substituent effects. Additionally, an interrupted variant of Fischer azaindolization methodology is disclosed, which provides a synthetic entryway into fused azaindoline scaffolds.

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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 42

ER -

Understanding and Interrupting the Fischer Azaindolization Reaction

Abstract

All Science Journal Classification (ASJC) codes

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