Synthesis of Novel Derivatives of pyrano[2,3-d]pyrimidinevia Intramolecular Cyclocondensation Reaction Under Acidic and Basic Conditions

Author(s): Ahmed Al-Sheikh, Kamal Sweidan, Munjed Ibrahim, Mohammed Alarjah, Norbert Kuhn.

Journal Name: Letters in Organic Chemistry

Volume 9 , Issue 6 , 2012

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Abstract:

In this study analogues of compounds based on pyrano[2,3-d]pyrimidine were synthesized. 1,3-dimethyl-5- (thiomethyl)-2,4,7-trioxo-1,3,4,7-tetrahydro-2H-pyrano[2,3-d]pyrimidine-6-carboxylic acid 3 and 1,3-dimethyl-5- (thiomethyl)-2H-pyrano[2,3-d]pyrimidine-2,4,7(1H,3H)-trione 4 were obtained by the treatment of Triethylammonium 5- [(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)(thiomethyl)methyl]-1,3-dimethylpyrimidine-2,4,6-trionate 1 with methyl sulfonic acid and pyridine, respectively. 5,5-dianilino-1,3-dimethyl-5,6-dihydro-2H-pyrano[2,3-d]pyrimidine- 2,4,7(1H,3H)-trione 6 was obtained after oxidizing compound 4 to produce 1,3-dimethyl-5-(methylsulfinyl)-2Hpyrano[ 2,3-d]pyrimidine-2,4,7(1H,3H)-trione 5 , then the sulfoxide group on compound 5 was replaced by aniline group.

Keywords: 1, 3-dimethylbarbituric acid, intramolecular cyclocondensation, meldrum's acid, pyrano[2, 3-d]pyrimidine, anti-bacterial, cardiotonic, antihypertensive, antifungal, antiallergic, analgesic activities

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Article Details

VOLUME: 9
ISSUE: 6
Year: 2012
Page: [386 - 389]
Pages: 4
DOI: 10.2174/157017812801322516
Price: $65

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