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A Variation of the Fischer Indolization Involving Condensation of Quinone Monoketals and Aliphatic Hydrazines
Author(s) -
Zhang Jinzhu,
Yin Zhiwei,
Leonard Patrick,
Wu Jing,
Sioson Kate,
Liu Che,
Lapo Robert,
Zheng Shengping
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201207533
Subject(s) - quinone , hydrazine (antidepressant) , condensation , indole test , chemistry , organic chemistry , phenols , physics , chromatography , thermodynamics
A new twist : A one‐pot nitrous acid free, diazonium‐free, and transition‐metal‐free variation of the Fischer indole synthesis has been developed. Condensation of quinone monoketals and aliphatic hydrazine hydrochlorides afforded indoles via intermediate alkylaryldiazenes. This method will complement the classical Fischer indole synthesis by providing indoles in two steps from widely available phenols under mild conditions.