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Molecules 2003, 8(5), 401-410; doi:10.3390/80500401
Article

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

1,*  and 1,2
Received: 26 November 2002; in revised form: 6 April 2003 / Accepted: 9 April 2003 / Published: 31 May 2003
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Abstract: 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.
Keywords: Quinazolinones; pyrroloquinazolinones; pyridazinoquinazolinones; N-aryl- maleimides; 3-aryl-2-cyanothioacrylamides; styrenes Quinazolinones; pyrroloquinazolinones; pyridazinoquinazolinones; N-aryl- maleimides; 3-aryl-2-cyanothioacrylamides; styrenes
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Ghabrial, S.S.; Gaber, H.M. Dipolar Cycloaddition Reactions with Quinazolinones: A New Route for the Synthesis of Several Annelated Pyrrolo- and Pyridazinoquinazoline Derivatives. Molecules 2003, 8, 401-410.

AMA Style

Ghabrial SS, Gaber HM. Dipolar Cycloaddition Reactions with Quinazolinones: A New Route for the Synthesis of Several Annelated Pyrrolo- and Pyridazinoquinazoline Derivatives. Molecules. 2003; 8(5):401-410.

Chicago/Turabian Style

Ghabrial, Sami S.; Gaber, Hatem M. 2003. "Dipolar Cycloaddition Reactions with Quinazolinones: A New Route for the Synthesis of Several Annelated Pyrrolo- and Pyridazinoquinazoline Derivatives." Molecules 8, no. 5: 401-410.


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