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Synthesis of 5,6-dihydrothieno(and furo)pyrimidines bearing an active methine group at the 4-position

✍ Scribed by Hiroshi Maruoka; Kenji Yamagata; Motoyoshi Yamazaki

Publisher
Journal of Heterocyclic Chemistry
Year
2001
Tongue
English
Weight
75 KB
Volume
38
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

The reactions of 2‐benzamido‐4,5‐dihydro‐3‐thiophene(and ‐3‐furan)carbonitriles (1a‐c and 4a‐c) with ethyl acetoacetate in the presence of tin(IV) chloride and triethylamine provided the corresponding ethyl 2‐(5,6‐dihydro‐2‐phenylthieno(and furo)[2,3‐d]pyrimidin‐4‐yl)‐3‐oxobutanoates (2a‐c and 9a‐c). Similarly, compounds 1a‐c and 4a‐c reacted with dialkyl malonates to give the corresponding dialkyl(5,6‐dihydro‐2‐phenylthieno(and furo)[2,3‐d]pyrimidin‐4‐yl)propanedioates (5a‐c, 6a‐c, 10a‐c and 11a‐c).

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