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Novel heterocycles. 9 . Synthesis of the benzofuro[2,3‐ c ][1,2]thiazine ring system
Author(s) -
Coppola Gary M.
Publication year - 1981
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.5570180448
Subject(s) - thiazine , chemistry , reagent , ring (chemistry) , d 1 , stereochemistry , medicinal chemistry , organic chemistry , biochemistry , receptor
The treatment of 2‐coumaranone with the Vilsmeier reagent affords three products: 2‐chloro‐3‐benzofurancarboxaldehyde ( 3 ), 3‐dimethylaminomethylene‐2‐(3 H )benzofuranone ( 4 ), and 3‐dimethylaminomethylene‐2,3‐dihydro‐2‐oxo‐6‐benzofurancarboxaldehyde ( 5 ). Both 4 and 5 are isolated as a mixture of E and Z isomers. The reaction of 3 with the anion of N ‐methylmethanesulfonamide affords the title compound 1‐methyl‐1 H ‐benzofuro[2,3‐ c ][1,2]‐thiazine 2,2‐dioxide ( 6 ). Spectral data is also discussed.