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Synthesis of 5-dienyl pyrimidinones and tandem [1,5] shifts in [4+2] cycloadditions of 1,3-diazabuta-1,3-dienes with butadienylketene

✍ Scribed by Arun K Sharma; S Jayakumar; Mohinder P Mahajan

Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 213 KB
Volume: 39
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(98)01553-6

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✦ Synopsis

The reactions of l-aryl-2-phenyl-4-methylthio-4-sccondaryamino / 4-N-allyl-N-aryl amino-1,3-diazabuta-l,3-dienes 1 with butadienylketene leading to a mixture of 5-dienyl pyrimidinones 4 and 5butenyl pyrimidinones 6 are reported. Tandem [1,5]H and [1,5]SMe shifts are invoked to explain fl~e formation of pyrimidinones 6.

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