Condensation of 2-Amino-5-chlorobenzoxazole with a-Bromoketones: A Mechanistic Study
Year: 1997
Type: article
Abstract: The condensation of 2-aminohenzothiazoles with a-bromo ketones produces the fused imidazothiazole (2) whereas the analogous reaction with 2aminohenzoxazoles gives the unexpected carbamate (10) or the fused imidazooxazole (13), depending on the nature of the starting materials.Isotope labelling studies as well as a proposed mechanism will be discussed.In a previous paper,' we discussed the synthesis and structure-activity relationship for a series of diarylimidazothiazole COX-2 inhibitors as represented by 1 ( Figure 1).During the course of that work, we decided to extend the series to include the benzo analogues (2) and (3).
Source: Heterocycles
DOI: 10.3987/com-97-7861
Institution: Merck & Co., Inc., Rahway, NJ, USA (United States)
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: diamond
OpenAlex ID: W1963782463