期刊
TETRAHEDRON
卷 68, 期 44, 页码 9035-9044出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2012.08.068
关键词
Electrophilic cyclization; Regioselective; Enolates; Diketoacid; Silver-catalyzed
资金
- Department of Science and Technology, New Delhi, India
- University of Delhi
- Council of Scientific and Industrial Research, New Delhi, India
A facile, efficient, and general synthetic method for a wide range of medicinally useful 2-carboxylate derivatives of acridinols, quinolinols, and naphthalenols has been developed via silver-catalyzed electrophilic cyclization of 3-(2-alkynyl)aryl-beta-ketoesters. The designed reaction involved selective C C bond formation on more electrophilic alkynyl carbon, which resulted in the regioselective 6-endo-dig cyclized product, as confirmed by X-ray crystallographic studies. The deuterium labeling experiments were performed to support the proposed mechanism. The synthetic methodology accommodates wide functional group variations on alkyne, which proves to be highly advantageous for structural and biological activity assessments. (C) 2012 Elsevier Ltd. All rights reserved.
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