In:
Advanced Synthesis & Catalysis, Wiley, Vol. 362, No. 17 ( 2020-09-08), p. 3635-3643
Abstract:
We have developed a palladium‐catalyzed cross‐coupling reaction of isocyanides with α‐diazoacetates to form active ketenimines and following a 1,4‐diazabicyclo[2.2.2]octane (DABCO) catalyzed aza‐Mannich type reaction with various 2‐mercaptoimidazoles for the synthesis of 1,3‐bis(β‐aminoacrylate)‐substituted 2‐mercaptoimidazole derivatives with structural diversity. In addition, the use of 1 H ‐benzo[ d ]imidazol‐2‐ol as the reaction partner also allowed the formation of 1,3‐bis(β‐aminoacrylate)‐substituted 2‐benzimidazolinone derivatives with moderate yields (34–52%). In the aza‐Mannich reaction, the regioselective N ‐attack rather than S ‐attack or O ‐attack at the electrophilic central carbon of ketenimines was observed. This tandem sequence is efficient since two C=C and two C−N bonds are consecutively created in one‐pot. magnified image
Type of Medium:
Online Resource
ISSN:
1615-4150
,
1615-4169
DOI:
10.1002/adsc.v362.17
DOI:
10.1002/adsc.202000789
Language:
English
Publisher:
Wiley
Publication Date:
2020
detail.hit.zdb_id:
2041384-1
detail.hit.zdb_id:
2033084-4
