1,3-Dipolar cycloaddition of azomethine imines to ethynyl hetarenes: A synthetic route to 2,3-dihydropyrazolo[1,2-a]pyrazol-1(5H)-one based heterobiaryls |
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Authors: | Julia I Nelina-Nemtseva Anna V Gulevskaya Vitaliy V Suslonov Alexander D Misharev |
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Institution: | 1. Department of Organic Chemistry, Southern Federal University, Zorge 7, Rostov-on-Don, 344090, Russian Federation;2. Center for X-ray Diffraction Studies and Chemical Analysis and Materials Research Centre, Saint Petersburg State University, Universitetskii Pr., 26, Peterhof, 198504, Russian Federation |
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Abstract: | π-Deficient ethynyl hetarenes were used as dipolarophiles in a 1,3-dipolar cycloaddition reaction with azomethine imines (2-arylidene-5-oxopyrazolidin-2-ium-1-ides). Both CuI-catalyzed and catalyst-free thermally induced reactions proceeded with high regioselectivity providing 6-hetaryl-5-aryl-2,3-dihydropyrazolo1,2-a]pyrazol-1(5H)-ones in moderate to excellent yields. The ethynyl hetarenes (pyridines, pyrazines, quinoxalines, pteridines and pyrimido4,5-c]pyridazines) with ortho-methyl, ortho-cyano and ortho-alkynyl substituents were applicable to this reaction. 1,3-Dipolar cycloaddition reactions of alkynyl hetarenes with azomethine imines or other 1,3-dipole reagents can be considered as an alternative synthetic approach to heterobiaryls. |
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Keywords: | 1 3-Dipolar cycloaddition Azomethine imines Ethynyl hetarenes Heterobiaryls BLOXNGHGDAAXJH-UHFFFAOYSA-N WWDBGQYTNYHCPX-UHFFFAOYSA-N OQDPSFGUOSZPSF-UHFFFAOYSA-N NJCCDYHRLLJXNB-UHFFFAOYSA-N LBUZVYXNFVECNC-UHFFFAOYSA-N ASDLNHAYVHSLCG-UHFFFAOYSA-N GMBOITURGPLREK-UHFFFAOYSA-N PCRLHDJHIBRIAK-UHFFFAOYSA-N HRPSROGUYINECB-UHFFFAOYSA-N WXOTXWUDZUHSMA-UHFFFAOYSA-N BBEFWQIAAZCEBF-UHFFFAOYSA-N JMOPWROWOXDGAI-UHFFFAOYSA-N TWIBAWKLTOIDRB-UHFFFAOYSA-N NMMSKKCVGGDPPY-UHFFFAOYSA-N FLAKQBRHSPTNDE-UHFFFAOYSA-N YMJGPRWNBDMRAU-UHFFFAOYSA-N WYVPHUSVJZEZPH-UHFFFAOYSA-N ADJKLWKTNZYJRU-UHFFFAOYSA-N LFQYSVLGKOPCRJ-UHFFFAOYSA-N MEQYZKGJBBXONM-UHFFFAOYSA-N CILUEEDVNBEYGJ-UHFFFAOYSA-N GKDHVIOIFVQTKB-UHFFFAOYSA-N ZTUNLKWJKLXKJN-UHFFFAOYSA-N |
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