Selective synthesis of 4-alkylidene-beta-lactams and N,N'-diarylamidines from azides and aryloxyacetyl chlorides via a ketenimine-participating one-pot cascade process.
A one-pot cascade approach to 4-alkylidene-beta-lactams and N, N'-diarylamidines from aryl azides and aryloxyacetyl chlorides has been developed. The chemical outcome of the reaction can be controlled selectively by an appropriate choice of the stoichiometric ratio of different substrates and reagents. The products should find use in pharmaceutical discovery, especially in the development of new antimicrobial agents against multidrug-resistant pathogens.
Yang
Yun-Yun
YY
Department of Chemistry, Zhejiang University, Hangzhou 310027, China.
Shou
Wang-Ge
WG
Hong
Deng
D
Wang
Yan-Guang
YG
D000085:Acetates / Q000737:chemistry*; D000215:Acylation; D000478:Alkylation; D000578:Amidines / Q000138:chemical synthesis* / Q000737:chemistry; D001386:Azides / Q000737:chemistry*; D002712:Chlorides / Q000737:chemistry*; D018360:Crystallography, X-Ray; D007649:Ketamine / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry*; D047090:beta-Lactams / Q000138:chemical synthesis* / Q000737:chemistry
D000085:Acetates; D000578:Amidines; D001386:Azides; D002712:Chlorides; D047090:beta-Lactams; D007649:Ketamine; C081124:acetyl chloride; D010100:Oxygen