A convenient synthesis and hepatoprotective activity of imidazo[1,2-c]pyrimido[5,4-e]pyrimidine, tetraazaacenaphthene and tetraazaphenalene from cyclic ketene aminals through tandem addition-cyclization reactions.

Abstract:

:A novel one-pot synthesis of imidazo[1,2-c]pyrimido[5,4-e]pyrimidinones (2), tetraazaacenaphthene-3,6-diones (4), tetarazaphenalene-1,7-dione (4d) is delineated from the reaction of cyclic ketene aminal (1) and alkyl or aryl isothiocyanate through tandem addition-cyclization reactions. However, reaction of ketene aminal (1a) with alkyl isothiocyanate only yielded angularly cyclized product 5 which did not react further to yield 6. The structure of 2c and 4d was ascertained by single crystal X-ray diffraction analysis which demonstrated a network of various inter- and intramolecular interactions, responsible for the stability and packing of the molecules in the crystalline state. Some of the compounds (2a--h) were screened for hepatoprotective activity but only 2a was found most effective.

journal_name

Bioorg Med Chem

authors

Ram VJ,Goel A,Sarkhel S,Maulik PR

doi

10.1016/s0968-0896(01)00423-0

subject

Has Abstract

pub_date

2002-05-01 00:00:00

pages

1275-80

issue

5

eissn

0968-0896

issn

1464-3391

pii

S0968089601004230

journal_volume

10

pub_type

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