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Alkylation of the 2H-5-nitro-2-acetonyl-4,6-dimethoxypyrimidine anion

✍ Scribed by G. Ya. Remennikov; V. M. Cherkasov; V. V. Pirozhenko

Publisher
Springer US
Year
1988
Tongue
English
Weight
69 KB
Volume
24
Category
Article
ISSN
0009-3122

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In the title compound, C 19 H 20 N 2 O 7 , the C atom in the 4position of the dihydropyridine ring is displaced out of the plane by 0.0461 (2) A ˚. The dihydropyridine ring plane is almost perpendicular to the benzene ring, with a dihedral angle of 88.9 (3) .

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The PPA induced Fischer indolization of 4-acetonyl-2,6-piperidinediones 4 takes place both at the methylene and the methyl carbons, although the latter regioisomer (3) undergoes a further cyclization of the imide moiety upon the indole 3position followed by ring-opening of the resulting intermediate

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Single-crystal X-ray study T = 293 K Mean '(C±C) = 0.003 A Ê R factor = 0.043 wR factor = 0.111 Data-to-parameter ratio = 12.9 For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.