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Reaction of sulfene with heterocyclic α‐dialkylaminomethyleneketones II. Synthesis of 5 N ‐1,2‐oxathiino[5,6‐ c ] [1]benzopyran derivatives
Author(s) -
Sche P.,
Morasso S.,
Bignardi G.
Publication year - 1972
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.5570090626
Subject(s) - chemistry , methylene , benzopyran , condensation , condensation reaction , medicinal chemistry , bicyclic molecule , organic chemistry , stereochemistry , catalysis , thermodynamics , physics
The reaction of sulfene with 3‐dialkylaminomethylene‐4‐chromanone and 3‐dialkylamino‐methylene‐6‐methyl‐4‐ehromanone gave 1,4‐cycloadducts which are derivatives of a new heterocyclic system, i.e. , 5 H ‐1,2‐oxathiino[5,6‐ c ][1]benzopyran. The structures of the adductswere determined by ir and nmr spectral data. Two new α‐hydroxymethyleneketones (3‐hydroxy‐methylene‐4‐chromanone and its 6‐methyl analogue) as well as some of their derived enamines were prepared. During the preparation of N,N ‐diethylenamines a self‐condensation occurs, which gives the byproducts Xa‐b.