Tetrahedron p. 6137 - 6142 (1988)
Update date:2022-07-30
Topics:
Baruah, Arpan K.
Prajapati, Dipak
Sandhu, Jagir S.
4H-1-Benzopyran-4-thione (1) reacted smoothly with nitrilimines (3a-e) to afford regioselective cycloadducts (4a-e) in good yields.In contrast,benzonitrile oxide (6) and aldonitrones (7a-d) reacted preferentially at the thione function.The unstable cycloadduct (8) or (9) ruptured to give as isolable products chromone (10) and phenyl isothiocyanate (11) and the thioamides (12a-d).This indirectly proves the site of attack of the dipole at the thione group.
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