Issue 6, 2002
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Tandem sigmatropic shifts in [4 + 2] cycloaddition reactions of 1,3-diazabuta-1,3-dienes with butadienylketene: synthesis of pyrimidinone derivatives

Arun K. Sharma,a   S. Jayakumar,b   Maninder S. Hundal†a  and  Mohinder P. Mahajan*a  

* Corresponding authors

a Department of Pharmaceutical Sciences, Guru Nanak Dev University, Amritsar-143005, India
E-mail: mohinderpmahajan@angelfire.com

b Department of Chemistry, Guru Nanak Dev University, Amritsar-143005, India

Abstract

The reactions of 4-dialkylamino substituted 1,3-diazabuta-1,3-dienes 1 with butadienylketene 2, are shown to undergo [4 + 2] cycloadditions to yield 5-(buta-1′,3′-dienyl)pyrimidinone 4 and tandem [1,5]H and [1,5]SCH3 shifts are shown to accompany the [4 + 2] cycloaddition reactions of 4-dialkylamino-4-methylthio substituted 1,3-diazabuta-1,3-dienes 5 with 2. The regioselective reactions of N-arylamino-1,3-diazabuta-1,3-dienes 11 and 14 with butadienylketene 2 are reported to yield 5-(buta-1′,3′-dienyl)-2-dialkylaminopyrimidin-4(3H)-one 13 and a mixture of 5-(buta-1′,3′-dienyl)-2-methylthiopyrimidin-4(3H)-one 17, 2-methylthio-5-[1′-(N-phenylamino)but-2′-enyl]pyrimidin-4(3H)-one 19 and 2-methylthio-5-[3′-(N-phenylamino)but-1′-enyl]pyrimidin-4(3H)-one 20, respectively. Tandem [1,5]H, [1,3]NHPh and [1,5]NHPh shifts are involved in the formation of pyrimidinones 19 and 20. The Diels–Alder reactions of the 5-dienylpyrimidinones with dimethyl acetylenedicarboxylate (DMAD) and 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) yielded corresponding cycloadducts.

Graphical abstract: Tandem sigmatropic shifts in [4 + 2] cycloaddition reactions of 1,3-diazabuta-1,3-dienes with butadienylketene: synthesis of pyrimidinone derivatives

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Article information

DOI
https://doi.org/10.1039/B109922C
Article type
Paper
Submitted
30 Oct 2001
Accepted
15 Jan 2002
First published
25 Feb 2002

J. Chem. Soc., Perkin Trans. 1, 2002, 774-784

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Tandem sigmatropic shifts in [4 + 2] cycloaddition reactions of 1,3-diazabuta-1,3-dienes with butadienylketene: synthesis of pyrimidinone derivatives

A. K. Sharma, S. Jayakumar, M. S. Hundal and M. P. Mahajan, J. Chem. Soc., Perkin Trans. 1, 2002, 774 DOI: 10.1039/B109922C

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