期刊
TETRAHEDRON
卷 73, 期 31, 页码 4663-4670出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2017.06.037
关键词
Azirines; Copper catalysis; Enols; Synthetic methods
资金
- Russian Foundation for Basic Research [16-03-00596, 16-33-60130]
- Saint Petersburg State University [12.38.217.2015]
A copper(I)-NHC-catalyzed annulation of 5-membered cyclic enols of furan, thiophene and indene family with 3-aryl-2H-azirines has been developed to provide a rapid access to furo[3,4-b]pyrrole, thieno[3,4-b] pyrrole, indeno[1,2-b]pyrrole derivatives. The reaction proceeds via a copper-initiated N-C-2 azirine bond cleavage with the retention of the C=N double bond in the annulation product. The reaction of tetronic acids with 3-aryl-2H-azirines can also proceed under catalyst-free conditions, through a double addition of the enol to the azirine, but this route provides poor yields of the annulation products. This is the first example of the N-C-2 bond cleavage in 2-unsubstituted 2H-azirines in the absence of a transition metal catalyst. (C) 2017 Elsevier Ltd. All rights reserved.
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