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Cyclocondensation of 3‐amino‐2‐iminonaphtho[1,2‐ d ]‐thiazole with α ‐ketocarboxylic acid derivatives: Synthesis of 2‐substituted 3‐Oxo‐3 H ‐naphtho[1′,2′:4,5]thiazolo‐[3,2‐ b ][1,2,4]triazines as potential anti‐HIV agents
Author(s) -
Liu KangChien,
Shih BiJane,
Lee ChuenHsiang
Publication year - 1992
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.5570290116
Subject(s) - chemistry , thiazole , acetic acid , medicinal chemistry , boiling , organic chemistry
The cyclocondensation of 3‐amino‐2‐iminonaphtho[1,2‐ d ]thiazole ( 1 ) with a series of α ‐keto mono‐ and dicarboxylic acid derivatives 5a‐i under different conditions was investigated. When the experiments were performed by refluxing in glacial acetic acid, the corresponding cyclized products, 2‐substituted 3‐oxo‐3 H ‐naphtho[1′,2′:4,5]thiazolo[3,2‐ b ][1,2,4]triazines 4 were obtained in fair to good yields. On the other hand, when the reaction was conducted in boiling ethanol, it gave only the open chain condensates 6 , or in rare cases, together with minor amount of 4 . Since the intermediates 6 exist as mixture of both E‐ and Z‐isomers, cyclization through heating was found insufficient. In any event representative compounds 4b,g,i have been evaluated for anti‐HIV activity, but none of them were active.