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Synthesis of Novel 3‐(3‐(5‐Methylisoxazol‐3‐yl)‐7 H ‐[1,2,4]Triazolo [3,4‐ b ][1,3,4]Thiadiazin‐6‐yl)‐2 H ‐Chromen‐2‐Ones
Author(s) -
Vaarla Krishnaiah,
Vedula Rajeswar Rao
Publication year - 2016
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.2301
Subject(s) - chemistry , isoxazole , coumarin , triazole , click chemistry , stereochemistry , medicinal chemistry , combinatorial chemistry , organic chemistry
A novel series of coumarin substituted triazolo‐thiadiazine derivatives were designed and synthesized by using 5‐methyl isoxazole‐3‐carboxylic acid ( 1 ), thiocarbohydrazide ( 2 ), and various substituted 3‐(2‐bromo acetyl) coumarins ( 4a , 4b , 4c , 4e , 4d , 4f , 4g , 4h , 4i , 4j ). Fusion of 5‐methyl isoxazole‐3‐carboxylic acid with thiocarbohydrazide resulted in the formation of the intermediate 4‐amino‐5‐(5‐methylisoxazol‐3‐yl)‐4 H ‐1,2,4‐triazole‐3‐thiol ( 3 ). This intermediate on further reaction with substituted 3‐(2‐bromo acetyl) coumarins under simple reaction conditions formed the title products 3‐(3‐(5‐methylisoxazol‐3‐yl)‐7 H ‐[1,2,4]triazolo[3,4‐b][1,3,4]thiadiazin‐6‐yl‐2 H ‐chromen‐2‐ones ( 5a , 5b , 5c , 5d , 5e , 5f , 5g , 5h , 5i , 5j ) in good to excellent yields. All the synthesized compounds were well characterized by physical, analytical, and spectroscopic techniques.