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Molecules 2015, 20(2), 1842-1859; doi:10.3390/molecules20021842

Microwave-Assisted Synthesis and Antimicrobial Evaluation of Novel Spiroisoquinoline and Spiropyrido[4,3-d]pyrimidine Derivatives

1
Chemistry Department, Faculty of Science, Cairo University, Cairo 12613, Egypt
2
Schlumberger, Well Services, Al-Khobar 31952, Saudi Arabia
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 27 December 2014 / Accepted: 20 January 2015 / Published: 23 January 2015
(This article belongs to the Section Organic Synthesis)
View Full-Text   |   Download PDF [775 KB, uploaded 23 January 2015]   |  

Abstract

Bromination of N-substituted homophthalimides and tetrahydropyrido[4,3-d]- pyrimidine-5,7-diones produces 4,4-dibromohomophthalimide and 8,8-dibromo-tetrahydropyrido[4,3-d]pyrimidine-5,7-dione derivatives, respectively, that can be used as precursors for spiro derivatives. The dibromo derivatives react with different binucleophilic reagents to produce several spiroisoquinoline and spirotetrahydropyrido[4,3-d]- pyrimidine-5,7-dione derivatives, respectively. Reaction of the dibromo derivatives with malononitrile produces dicyanomethylene derivatives which react with different binucleophiles to produce new spiro derivatives. All new compounds are prepared by using the usual chemical conditions and microwave assisted conditions. The latter conditions improved the reaction yields, reduced reaction times and ameliorated the effects on the surrounding environment as the reactions are carried out in closed systems. Structures of the newly synthesized compounds are proved using spectroscopic methods such as IR, MS, 1H-NMR and 13C-NMR and elemental analyses. Some of the newly synthesized compounds were tested for their antimicrobial activities, whereby four of them showed moderate activities and the rest showed low or no activities towards the investigated species. View Full-Text
Keywords: bromination; homophthalimide; pyrido[4,3-d]pyrimidine; spiro compounds; microwave; antimicrobial bromination; homophthalimide; pyrido[4,3-d]pyrimidine; spiro compounds; microwave; antimicrobial
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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. (CC BY 4.0).

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MDPI and ACS Style

Faty, R.M.; Rashed, M.S.; Youssef, M.M. Microwave-Assisted Synthesis and Antimicrobial Evaluation of Novel Spiroisoquinoline and Spiropyrido[4,3-d]pyrimidine Derivatives. Molecules 2015, 20, 1842-1859.

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