An expeditious synthesis of 6-Amido-(1H,3H)-Pyrimidine- 2,4-Diones from Uracil-6-Carboxylic Acid

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Two-Step Synthetic Approach to 6-Substituted Pyrido[2,3-d]pyrimidine(1H,3H)-2,4-diones from 6-Amino-, 6-Alkylamino-, and 6-Arylamino-1,3-dimethyluracils*

The Mannich reaction of 7-aryl-5,6-dihydropyrido[2,3-d]pyrimidines 3, easily accessible by condensation of 6-amino-1,3-dimethyluracil (1) with Mannich bases 2a – c, gives rise to a mixture of 7-aryl-6-(N,N-dimethylaminomethyl)pyrido[2,3-d]pyrimidines 6 and 7 as well as 1,2-bis(7-arylpyrido[2,3-d]pyrimidin-6-yl)ethane 13 the ratio of which depends on the reaction conditions and the amine used. 6...

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T3P/DMSO is shown to be an effective and mild reagent for the one-pot synthesis of furo[2,3-d]pyrimidine-2,4(1H,3H)-diones from a variety of alcohols. Alcohols are oxidized in situ to aldehydes under mild conditions, which undergo a three-component reaction with N,N'-dimethylbarbituric acid and various isocyanides to afford furo[2,3-d]pyrimidine-2,4(1H,3H)-diones in good yields.

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(2RS,8aRS)-6-Oxo-1,2,3,4,6,7,8,8a-octa­hydro­naphthalene-2-carboxylic acid

The title racemate, C(11)H(14)O(3), aggregates in the crystal structure as acid-to-ketone O-H⋯O hydrogen-bonding catemers whose components are glide-related. The relative stereochemistry at the carboxyl group arises spontaneously during the synthesis. Two inter-molecular C-H⋯O=C close contacts were found, both involving the acid group.

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ژورنال

عنوان ژورنال: Dhaka University Journal of Pharmaceutical Sciences

سال: 2015

ISSN: 1816-1839,1816-1820

DOI: 10.3329/dujps.v13i1.21856