Journal
TETRAHEDRON LETTERS
Volume 50, Issue 40, Pages 5617-5621Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2009.07.113
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Funding
- National Medical Research Council, Singapore [NMRC/NIG/0020/2008]
- National University of Singapore [R-148-050-091-101/133]
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A practical synthesis of pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidines, which are key intermediates in the preparation of adenosine receptor antagonists, is developed. The method allows introduction of a variety of aryl substituents at position 2 of the pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine system via cyclocondensation of 5-amino-4-iminopyrazolo[3,4-d]pyrimidine with benzaldehydes accompanied with oxidation by iodobenzene diacetate. Some unexpected reactions are observed and the structures of the products are confirmed using NMR spectroscopy and X-ray crystallography. (C) 2009 Elsevier Ltd. All rights reserved.
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