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Regioselective synthesis of polysubstituted 3,3′-bi-1H-pyrazole derivatives via 1,3-dipolar cycloaddition reactions

✍ Scribed by Ahmad M. Farag; Nabila A. Kheder; Milos Budesinsky

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
363 KB
Volume
53
Category
Article
ISSN
0040-4020

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✦ Synopsis

N,N'-Diarylbisnitrile imides 2 add regioselectively to ¢t-(benzothiazol-2-yl)cinnamonitriles 3 and ct-(l-methylbenzimidazol-2-yl)cinnamonitriles 7 to yield exclusively the cycloadducts 5,5'-dicyano-4,4',5,5'-tetrahydro[3,3'-bi-lH-pyrazoles] 4 and 8, respectively. Compounds 4 and 8 undergo aromatization via thermal elimination of hydrogen cyanide under basic conditions to afford the corresponding 3,3'-bi-lH-pyrazole derivatives 6 and 10, respectively. The regiochemistry of the cycloadduets is discussed.

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