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Synlett 2001; 2001(8): 1299-1301
DOI: 10.1055/s-2001-16036
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Studies on 6-[(Dimethylamino)methylene]aminouracils: a Facile One-pot Synthesis of Pyrimido[4,5-d]pyrimidines and Pyrido[2,3-d]pyrimidines.

Ashim J. Thakur* , Promod Saikia, Dipak Prajapati, Jagir S. Sandhu
  • *Department of Organic Chemistry (Drugs) Regional Research Laboratory, Jorhat 785006, Assam, India; Fax + 91 0376 37 01 16 or + 91 0376 37 00 11; E-mail: drrljt@csir.res.in
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Publication Date:
31 December 2001 (online)

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6-[(Dimethylamino)methylene]amino-1,3-dimethyl uracil 1 undergoes formal [4 + 2] cycloaddition reaction with nonconjugated imines to give pyrimido[4,5-d]pyrimidines 3. When reacted with conjugated imines and α,β-unsaturated nitro compounds cycloaddition also occurs leading to unexpected pyrido[2,3-d]pyrimidines 5 and 9, respectively.

pyrimido[4,5-d]pyrimidines - pyrido[2,3-d]pyrimidines - imines - α,β-unsaturated nitro compounds and β-nitrostyrenes