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Synthesis 1995; 1995(7): 863-867
DOI: 10.1055/s-1995-3989
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Imidazo[1’,2’:3,4]pyrimido[6,1-a]isoquinoline and Pyrimido[1’,2’:3,4]pyrimido[6,1-a]isoquinoline Ring Systems by Tandem Cyclization

Ferenc Fülöp* , Heinrich Wamhoff, Pál Sohár
  • *Institute of Pharmaceutical Chemistry, Albert Szent-Györgyi Medical University, H-6701 Szeged, POB 121, Hungary, Fax +36(62)310604; E-mail FULOP@pharma.szote.u-szeged.hu
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Publication Date:
31 December 2000 (online)

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The reactions of 6,7-dialkoxy-1,2,3,4-tetrahydroisoquinoline-1-acetonitriles 3 and 4 with 2-chloroethyl and 3-chloropropyl isocyanates resulted in ureas 5-8, which were transformed with sodium methylate into the new ring systems 9,10-dimethoxy- and 9,10-diethoxy-5H-2,3,7,8,12b,13-hexahydroimidazo[1’,2’:3,4]pyrimido[6,1-a]isoquinolin-5-one (9, 10) and 11,12-dimethoxy- and 11,12-diethoxy-2H,6H-3,4,8,9,13b,14-hexahydropyrimido[1’,2’:3,4]pyrimido[6,1-a]isoquinoline-6-one (11, 12) by tandem cyclization.

2-chloralkyl isocyanates - imidazo[1’,2’:3,4]pyrimido[6,1-a]isoquinoline - pyrimido[1’,2’:3,4]pyrimido[6,1-a]isoquinoline - new ring systems - tandem cyclization