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    Regioselective synthesis of pyrimido [1,2-a][1,3,5]triazin-6-ones via reaction of 1-(6-oxo-1,6-dihydropyrimidin-2-yl)guanidines with triethylorthoacetate: Observation of an unexpected rearrangement

    185942_185942 full.pdf (545.3Kb)
    Access Status
    Open access
    Authors
    Sachdeva, N.
    Dolzhenko, Anton
    Chui, W.
    Date
    2012
    Type
    Journal Article
    
    Metadata
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    Citation
    Sachdeva, Nikhil and Dolzhenko, Anton and Chui, Wai Keung. 2012. Regioselective synthesis of pyrimido [1,2-a][1,3,5]triazin-6-ones via reaction of 1-(6-oxo-1,6-dihydropyrimidin-2-yl)guanidines with triethylorthoacetate: Observation of an unexpected rearrangement. Organic & Biomolecular Chemistry. 10 (23): pp. 4586-4596.
    Source Title
    Organic & Biomolecular Chemistry
    DOI
    10.1039/C2OB25195G
    ISSN
    14770520
    School
    School of Pharmacy
    URI
    http://hdl.handle.net/20.500.11937/10305
    Collection
    • Curtin Research Publications
    Abstract

    A novel thermal rearrangement, involving pyrimidine ring opening and subsequent ring closure leading to recyclization of the system, was identified in the reaction of (6-oxo-1,6- dihydropyrimidin-2-yl)guanidines 3 (where NR1R2 = NH2, NH alkyl, NH aralkyl, NHCH2Ph(R)) with triethyl orthoacetate, affording 4-substituted-2-methyl-6H-pyrimido[1,2-a][1,3,5]triazin-6- ones 6 and their ring opened products. However, no such rearrangement was observed with (6- oxo-1,6-dihydropyrimidin-2-yl)guanidines 3 bearing a tertiary amino or anilino substituent (i.e. where NR1R2 = N(CH3)2, indoline, morpholino, NHAr). As expected, 2-substituted-4-methyl- 6H-pyrimido[1,2-a][1,3,5]triazin-6-ones 4 were obtained as the final products. Experimental 2 structural determination and theoretical studies were carried out to get an understanding of the observed thermal rearrangement. In addition, an attempt to obtain similar pyrimido[1,2-a][1,3,5]triazin-6-ones using N,N-dimethylacetamide dimethyl acetal (DMA-DMA) as one carbon inserting synthon had furnished triazine ring annulated product 14 bearing N,N-dimethyl enamino substituent at position 4 as a result of further reaction with a second molecule of DMA-DMA.

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