Journal
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
Volume 189, Issue 6, Pages 839-848Publisher
TAYLOR & FRANCIS LTD
DOI: 10.1080/10426507.2013.858253
Keywords
DMAP; benzenesulfonamides; pyrrolo[2,3-d]pyrimidin-4-amines; solvent-free conditions
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Funding
- Islamic Azad University, Mashhad Branch
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4-(N,N-Dimethylamino)pyridine (DMAP), with a dual role as a basic nucleophilic catalyst, was shown to be a highly efficient catalyst for the synthesis of some new N-(2-aryl-7-benzyl-5,6-diphenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)benzenesulfonamides through the reaction of 2-aryl-7-benzyl-5,6-diphenyl-7H-pyrrolo[2,3-d]pyrimidin-4-amines (7-deazaadenines) with benzenesulfonyl chlorides. It was also found that the use of DMAP under solvent-free conditions is much more effective than other catalytic systems such as pyridine as both the catalyst and solvent, t-BuOK in t-BuOH, Et3N in ethanol (EtOH), and even DMAP in dimethylformamide (DMF). The influences of the reaction parameters, temperature, and the catalyst amount, on the catalytic performance have been studied. All synthetic compounds were characterized on the basis of their full spectral data.
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