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Synthesis of New Pyrazolo[3,4‐b]quinolines, Thieno[2,3‐b]quinolines and Related Condensed Heterocyclic Systems
Author(s) -
Bakhite Etify AbdelGhafar
Publication year - 2001
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.200100173
Subject(s) - chemistry , quinoline , phenyl isothiocyanate , methylene , isothiocyanate , acetylacetone , benzaldehyde , hydroxylamine , acetic acid , medicinal chemistry , carbohydrazide , stereochemistry , organic chemistry , combinatorial chemistry , catalysis
3‐Amino‐1 H ‐pyrazolo[3,4‐b]quinoline ( 2 ) was reacted with benzaldehyde, acetylacetone, ethylacetoacetate and/or phenyl isothiocyanate to give compounds 3,4,5 and 6 , respectively. The interaction of 6 with some α‐haloesters and/or α‐haloketones produced the corresponding thiazolidinones 7a‐c and thiazolines 9a‐d . 1 H ‐Pyrazolo[3,4‐b]quinoline‐3‐diazonium chloride ( 11 ) was coupled with some active methylene compounds to give the corresponding hydrazono compounds 12a,b and 13 which, in turn were cyclized into the corresponding triazinopyrazoloquinolines 14a,b and 15 by heating in acetic acid. 3‐Aminothieno[2,3‐b] quinoline‐2‐carbohydrazide ( 19 ) and 3‐amino‐2‐(1 H ‐benzimidazol‐2‐yl)thieno[2,3‐b]quinoline ( 21 ) were prepared and employed as key intermediates for synthesizing the second class of the title compounds.