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Synthesis of representative 10‐aryl‐, 10‐aralkyl‐ and 10‐heteraryl‐9 H ‐naphtho[1′,2′:4,5]thiazolo[3,2‐ b ]‐ [1,2,4]triazin‐9‐ones as potential anti‐HIV agents
Author(s) -
Liu KangChien,
Shih BiJane,
Lee ChuenHsiang
Publication year - 1993
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.5570300525
Subject(s) - chemistry , glyoxylic acid , yield (engineering) , acetic acid , thiazole , methanol , aryl , medicinal chemistry , stereochemistry , organic chemistry , materials science , alkyl , metallurgy
To prepare the title compounds, cyclocondensation of 1‐amino‐2‐iminonaphtho[1,2‐ d ]thiazole ( 2 ) with some representative glyoxylic acid derivatives was investigated. Heating 2 with methyl phenylglyoxylate ( 3a ) in methanol afforded only the open chain intermediates 4a,b . However, when this reaction was performed in re‐fluxing glacial acetic acid, the expected compound, 10‐phenyl‐9 H ‐naphtho[1′,2′:4,5]thiazolo[3,2‐ b ][1,2,4]‐ triazin‐9‐one ( 5a ) was produced in 27% yield. Similar treatment of 2 with benzyl‐, 2‐furyl‐ and 2‐thienylgly‐oxylic acids 3b‐d gave the corresponding 10‐benzyl‐, 10‐(2‐furyl)‐ and 10‐(2‐thienyl)‐9 H ‐naphtho[1′,2′:4,5]thi‐azolo[3,2‐ b ][1,2,4]triazin‐9‐ones 5b‐d in 48–67% yields. As by‐products, 9‐benzoyl‐ and 9‐(2‐thenoyl)naphtho‐[1′,2′:4,5]thiazolo[3,2‐ b ][1,2,4]triazoles 6a,d were also isolated. Compound 5a was selected for in vitro anti‐HIV evaluation but found to be inactive.