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[3+1+1] Annulation Reaction of Benzo‐1,2‐Quinones, Aldehydes and Hydroxylamine Hydrochloride: Access to Benzoxazoles with Inorganic Nitrogen Source
Author(s) -
Chen Fulin,
Zhu Chuanle,
Jiang Huanfeng
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202001521
Subject(s) - chemistry , hydroxylamine hydrochloride , annulation , hydroxylamine , oxime , aldehyde , hydrochloride , organic chemistry , nitrogen , medicinal chemistry , catalysis
A synthesis of benzoxazoles with an inorganic nitrogen source is reported. By employing large‐tonnage industrial feedstock inorganic hydroxylamine hydrochloride as the nitrogen source, its [3+1+1] annulation reaction with benzo‐1,2‐quinones and aldehydes delivers various useful benzoxazoles in high yields. Preliminary mechanistic studies prove that the quinone oxime rather than the aldehyde oxime is the reaction intermediate.