Dipolar Cycloaddition Reactions with Quinazolinones: A New Route for the Synthesis of Several Annelated Pyrrolo- and Pyridazinoquinazoline Derivatives

The novel 2-aryl-3a,4,12,12a-tetrahydropyrrolo[3',4':4,3]-pyridazino[6,1-b]-quinazoline-1,3,6-triones (6a–d), 2-aryl-10-oxopyridazino[6,1-b]-quinazoline-3-thio-carboxamides (10a–d) and 2-aryl-3-nitro-1,2,3,4-tetrahydro-pyridazino[6,1-b]quinazolin-10-ones (12a–d) were synthesized via a new,...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2003-05, Vol.8 (5), p.401-410
Main Authors: Ghabrial, Sami S., Gaber, Hatem M.
Format: Article
Language:English
Subjects:
3-aryl-2-cyanothioacrylamides
Anticonvulsants
Biological activity
N-aryl- maleimides
pyridazinoquinazolinones
pyrroloquinazolinones
Quinazolinones
styrenes
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Summary:The novel 2-aryl-3a,4,12,12a-tetrahydropyrrolo[3',4':4,3]-pyridazino[6,1-b]-quinazoline-1,3,6-triones (6a–d), 2-aryl-10-oxopyridazino[6,1-b]-quinazoline-3-thio-carboxamides (10a–d) and 2-aryl-3-nitro-1,2,3,4-tetrahydro-pyridazino[6,1-b]quinazolin-10-ones (12a–d) were synthesized via a new, facile one step route involving the reactions of the zwitterion 4, formed in situ, with a variety of N-arylmaleimides 5, 3-aryl-2-cyano-thioacrylamides 8 and ω-nitrostyrenes 11. Dehydrogenation of the tetrahydro derivatives 6a–d and 12a–d in nitrobenzene resulted in the formation of 2-arylpyrrolo[3',4':4,3]-pyridazino[6,1-b]quinazoline-1,3,6-triones (7a–d) and 2-aryl-3-nitropyridazino[6,1-b]quinazolin-10-ones (13a–d), respectively. The structures of the products were confirmed by elemental analysis and spectral data.
ISSN:1420-3049
1420-3049
DOI:10.3390/80500401