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Synthesis of α‐Aminocyclopropyl Ketones and 2‐Substituted Benzoimidazoles from 2‐Hydroxycyclobutanones and Aryl Amines
Author(s) -
Serusi Lorenzo,
Soddu Francesco,
Cuccu Federico,
Peretti Giuseppe,
Luridiana Alberto,
Secci Francesco,
Caboni Pierluigi,
Aitken David J.,
Frongia Angelo
Publication year - 2020
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.202000541
Subject(s) - chemistry , aromatization , aryl , ring (chemistry) , catalysis , closure (psychology) , medicinal chemistry , combinatorial chemistry , organic chemistry , alkyl , economics , market economy
We have developed one‐step protocols for the preparation of a large selection of α‐aminocyclopropyl ketones or benzo[d]imidazoles, by reacting 2‐substituted‐2‐hydroxycyclobutanones with aryl amines or o ‐phenylenediamines, respectively. In most case the reactions proceed at room temperature and are catalyst‐free. The formation of benzo[d]imidazoles is rationalized in terms of an unusual ring‐closure/ring‐fission process followed by aromatization.