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Preparation of novel heterocyclic systems from isatoic anhydrides
Author(s) -
Sunder Shyam,
Peet Norton P.
Publication year - 1979
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.5570160710
Subject(s) - chemistry , thionyl chloride , trifluoroacetic anhydride , carbon disulfide , potassium carbonate , trifluoroacetic acid , medicinal chemistry , phosphoryl chloride , organic chemistry , chloride , acetic anhydride , acetyl chloride , catalysis
Isatoic anhydride ( 1a ) and 5‐chloroisatoic anhydride ( 1b ) were treated with 2‐(1‐methylhydrazino)ethanol ( 2 ) to produce 2‐aminobenzoic acid 2‐(2‐hydroxyethyl)‐2‐methylhydrazide ( 3a ) and its 5‐chloro analog 3b , respectively. Treatment of 3a and 3b with carbon disulfide gave, respectively, 2,3‐dihydro‐3‐[(2‐hydroxyethyl)methylamino]‐2‐thioxo‐4‐(1 H )quinazolinone ( 4a ) and its 6‐chloro analog 4b . Compounds 4a and 4b afforded 5,6‐dihydro‐5‐methyl‐2‐thioxo‐4 H ,8 H ‐[1,3,5,6]oxathiadiazocino[4,5‐ b ]quinazolin‐8‐one ( 5a ) and its 10‐chloro analog 5b , respectively, upon treatment with thiophosgene. Compound 5a could be produced directly from 3a and thiophosgene. Treatment of 4a and 4b with trifluoroacetic anhydride followed by potassium carbonate gave 3,4‐dihydro‐4‐methyl‐2 H ,6 H ‐[1,3,4]thiadiazino[2,3‐ b ]quinazolin‐6‐one ( 7a ) and its 8‐chloro analog 7b , respectively. Treatment of 4a with thionyl chloride also gave 7a , but 4b and thionyl chloride afforded a mixture of 7b and 8‐chloro‐3,4‐dihydro‐4‐methyl‐2 H ,6 H ‐[1,3,4]oxadiazino[2,3‐ b ]quinazolin‐6‐one ( 10 ). The dimethyl analogs of 4a and 4b ( 13a and 13b ) upon treatment with thiophosgene afforded 3,4‐dihydro‐2,2,4‐trimethyl‐2 H ,6 H ‐[1,3,4]oxadiazino[2,3‐ b ]quinazolin‐6‐one ( 14a ) and its 8‐chloro analog 14b , respectively.