Selective synthesis of 4-alkylidene-beta-lactams and N,N'-diarylamidines from azides and aryloxyacetyl chlorides via a ketenimine-participating one-pot cascade process | Health & Environmental Research Online (HERO)

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Citation
Tags

HERO ID

658208

Reference Type

Journal Article

Title

Selective synthesis of 4-alkylidene-beta-lactams and N,N'-diarylamidines from azides and aryloxyacetyl chlorides via a ketenimine-participating one-pot cascade process

Author(s)

Yang, YY; Shou, WG; Hong, D; Wang, YG

Year

2008

Is Peer Reviewed?

Yes

Journal

Journal of Organic Chemistry
ISSN: 0022-3263
EISSN: 1520-6904

Volume

Issue

Page Numbers

3574-3577

Language

English

PMID

18363365

DOI

10.1021/jo702733

Web of Science Id

WOS:000255339600037

Abstract

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.

Keywords

Acetic Acids/ chemistry; Acylation; Alkylation; Amidines/ chemical synthesis/chemistry; Azides/ chemistry; Chlorides/ chemistry; Crystallography, X-Ray; Ketamine/ chemistry; Models, Molecular; Molecular Structure; Oxygen/ chemistry; beta-Lactams/ chemical synthesis/chemistry