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Synthesis of substituted 2‐amino‐3‐cyanodihydrofurans from styrene oxides and malononitrile
Author(s) -
Campaigne E.,
Ellis R. L.,
Bradford Mary
Publication year - 1969
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.5570060203
Subject(s) - malononitrile , chemistry , steric effects , styrene , aryl , oxide , medicinal chemistry , dehydration , ion , organic chemistry , polymer chemistry , catalysis , copolymer , biochemistry , alkyl , polymer
The reaction of styrene oxides with the malononitrile anion leads to the formation of 2‐amino‐3‐eyano‐5‐aryl‐4,5‐dihydrofurans (III), while a similar reaction with β,β‐dimethylstyrene oxides leads to 2‐amino‐3‐cyano‐4‐aryl‐5,5‐dimethyI‐4,5‐dihydrofurans (V). Therefore steric factors may play a significant role in the site of attack of the malononitrile anion on the oxide. Compounds of type V are more conveniently obtained from the cyanolaetones (VI) by rearrangement and dehydration.