Benzoquinolines II. Synthesis of some new benzo[h] pyrimido [4′,5′:4,5]thieno[2,3-b]quinoline derivatives and related fused hexacyclic systems

Article abstract of DOI:10.1080/10426500008043660

Reaction of 8-amino-7-(2 furyl)-5,6-dihydrobenzo[h]thieno[2,3-b]quinoline-9-carbonitrile (3a) with phenyl isothiocyanate, triethyl orthoformate, ethylenediamine and/or sodium azide afforded benzo[h]thieno[2,3-b]quinolines 4, 7, 20 and 25 respectively. Cyclization of thiourea derivative 4 furnished thioxopyrimidine derivative 5. The dithioxopyrimidine 6 was prepared by reaction of 3a with carbon disulfide. On treatment of 7 with hydrazine hydrate, 10-amino-7-(2-furyl)-11-imino-5,6,10,11-tetrahydrobenzo[h]pyrimido[4′,5′:4,5]thieno [2,3-b]quinoline (8) was obtained. Compounds 8, 20 and 25 were used as key intermediates in the synthesis of the fused hexacyclic compounds 9-19, 21-24 and 26-28 respectively. 8-Amino-7-(2-furyl)-5,6-dihydrobenzo[h]thieno[2,3-b]quinoline-9-carboxamide (3b) was reacted with some reagents, namely triethyl orthoformate, benzaldehyde, carbon disulfide, phenyl isothiocyanate, and/or acetic anhydride to give the corresponding benzo[h]pyrimido [4′,5′: 4,5]thieno[2,3-b]quinolines 29, 30, 31, 32 and 34. Compound 29 underwent some sequence reactions to give 37-42. Some of the prepared compounds were tested in vitro for their antibacterial and antifungal activities.

Full text of DOI:10.1080/10426500008043660

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Phosphorus, Sulfur, and Silicon
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BENZOQUINOLINES II.
SYNTHESIS OF SOME
NEW BENZO[h] PYRIMIDO
[4′,5′:4,5]THIENO[2,3-
b]QUINOLINE DERIVATIVES AND
RELATED FUSED HEXACYCLIC
SYSTEMS
Etify Abdel-Ghafar Bakhite a
a Chemistry Department, Faculty of Science, Assiut
University, Assiut, 71516, Egypt
Version of record first published: 04 Oct 2006.
To cite this article: Etify Abdel-Ghafar Bakhite (2000): BENZOQUINOLINES II.
SYNTHESIS OF SOME NEW BENZO[h] PYRIMIDO [4′,5′:4,5]THIENO[2,3-b]QUINOLINE
DERIVATIVES AND RELATED FUSED HEXACYCLIC SYSTEMS, Phosphorus, Sulfur, and
Silicon and the Related Elements, 159:1, 171-194
To link to this article: http://dx.doi.org/10.1080/10426500008043660
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