Journal of Heterocyclic Chemistry p. 743 - 749 (2002)
Update date:2022-09-26
Topics:
Maruoka, Hiroshi
Yamazaki, Motoyoshi
Tomioka, Yukihiko
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 e 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 dihydrofuro[2,3-b]pyridines 11a-c.
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