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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
Author(s) -
Maruoka Hiroshi,
Yamazaki Motoyoshi,
Tomioka Yukihiko
Publication year - 2002
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570390420
Subject(s) - chemistry , sodium ethoxide , alkoxide , yield (engineering) , adduct , medicinal chemistry , sodium , potassium , stereochemistry , organic chemistry , catalysis , ethanol , materials science , metallurgy
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 .