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Room‐Temperature, Metal‐Free, and One‐Pot Preparation of 2 H ‐Indazoles through a Mills Reaction and Cyclization Sequence
Author(s) -
Kondo Masaru,
Takizawa Shinobu,
Jiang Yuzhao,
Sasai Hiroaki
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201902242
Subject(s) - indazole , chemistry , sequence (biology) , acetic acid , bromide , metal , organic chemistry , combinatorial chemistry , medicinal chemistry , biochemistry
The Mills reaction and cyclization of readily available 2‐aminobenzyl alcohols and nitrosobenzenes using thionyl bromide provided 2 H ‐indazoles in up to 88 % yields. In the metal‐free process, acetic acid played a crucial role for the both Mills reaction and cyclization. A brominated 2 H ‐indazole could also be obtained through the one‐pot sequence.