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A convenient synthesis of 3‐alkyl‐2,3‐dihydro‐2,4‐dioxo‐6‐phenyl‐, 3‐alkyl‐2,3‐dihydro‐4‐oxo‐6‐phenyl‐2‐thioxo‐, and 3‐alkyl‐2‐arylimino‐2,3‐dihydro‐4‐oxo‐6‐phenyl‐4 H ‐1,3‐thiazines
Author(s) -
Kim Sung Hoon,
Ra Yong Hoon,
Lee Yoon Young,
Kim Kyongtae,
Kim Joong Hyup
Publication year - 1994
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.5570310611
Subject(s) - chemistry , triethylamine , alkyl , toluene , oxalyl chloride , phosgene , medicinal chemistry , benzene , organic chemistry
The reactions of 1‐alkylamino‐1‐alkylthio‐3‐phenylpropene‐3‐thiones 3 with thiophosgene and phosgene in toluene, followed by treatment of the reaction mixture with triethylamine gave 3‐alkyl‐2,3‐dihydro‐4‐oxo‐6‐phenyl‐2‐thioxo‐ 4 , 3‐alkyl‐2,3‐dihydro‐2,4‐dioxo‐6‐phenyl‐4 H ‐1,3‐thiazines 5 , respectively in good to excellent yields. Similarly treatment of compounds 3 with N ‐arylimidoyl dichloride in benzene at room temperature gave 3‐alkyl‐2‐arylimino‐2,3‐dihydro‐4‐oxo‐6‐phenyl‐4 H ‐1,3‐thiazines 6 in excellent yields. The reactions of compounds 3 with oxalyl chloride in toluene gave also 5 in good yields.