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Synthesis of dihydrofuro[2,3-b]pyridines by the reaction of 2-amino-4,5-dihydro-3-furancarbonitriles with α,β-unsaturated carbonyl compounds

✍ Scribed by Hiroshi Maruoka; Motoyoshi Yamazaki; Yukihiko Tomioka

Publisher
Journal of Heterocyclic Chemistry
Year
2002
Tongue
English
Weight
60 KB
Volume
39
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

The reactions of 2‐amino‐4,5‐dihydro‐3‐furancarbonitriles 1a‐d with α,β‐unsaturated carbonyl compounds in the presence of sodium ethoxide (0.1 equivalent) gave the corresponding Michael adducts 2a‐d, 3a‐d and 4a‐d. Compounds 2a‐d and 3a‐c reacted with sodium alkoxide (1 equivalent) to yield the corresponding 7a‐alkoxyhexahydrofuro[2,3‐b]pyridines 5a‐d, 6a‐d, 7a‐c and 8a‐c. Treatment of 5a‐d, 6a‐d, 7a‐c and 8a‐c with potassium tert‐butoxide produced the corresponding dihydrofuro[2,3‐b]pyridines 9a‐d and 10a‐c. The reaction of 4a‐c with sodium ethoxide (1 equivalent) afforded the corresponding dihydro‐furo[2,3‐b]pyridines 11a‐c.

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Synthesis of dihydrothieno[2,3-b]pyridin
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