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Synthesis 2001(10): 1568-1572
DOI: 10.1055/s-2001-16097
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Bioactive Heterocycles: Sigmatropic Rearrangements of 1,3-Dimethyl-6-[methyl(4-aryloxybut-2-ynyl)amino]pyrimidine-2,4(1H,3H)-diones

K. C. Majumdar*, T. Bhattacharyya
Department of Chemistry, University of Kalyani, Kalyani 741 235, W.B., India
Fax: +91(033)5828282; e-Mail: kcm@klyuniv.ernet.in;
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Publikationsverlauf

Received 13 March 2001
Publikationsdatum:
29. September 2004 (online)

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Abstract

A number of 1,3-dimethyl-6-[methyl(4-aryloxybut-2-ynyl)amino]pyrimidine-2,4(1H,3H)-diones 4a-i were synthesised in 69 to 80% yields by the reaction of 6-chloro-1,3-dimethyluracil (6-chloro-1,3-dimethylpyrimidine-2,4(1H,3H)-diones) and 1-aryloxy-4-N-methylaminobut-2-yne in refluxing ethanol for 12 hours. The tertiary amines 4a-i were then heated in refluxing 1,2-dichlorobenzene for 17 hours to give 5-[(E)-aryloxymethylidene]-1,3,8-trimethyl-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidine-2,4(1H,3H)-diones 5a-i in 55 to 75% yields.

Key words

aza-Claisen rearrangement - cyclizations - heterocycles - pyrido[2,3-d]pyrimidine-2,4-diones - sigmatropic rearrangement

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