Stereochemical studies. Part 103. Saturated heterocycles part 107. Preparation of 3-mono- and 2,3-di-substituted pyrimidin-4(3H)-ones in retro-diels-alder reactions. the correct 1,2-disubstituted structure of the compounds previously described as 2,3-disubstituted derivatives

G. Stájer, Angela E. Szabó, G. Bernáth, P. Sohár

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Abstract

The orthoformate cyclization of carboxamides (4) obtained from 3-exo-aminobicyclo[2.2.1]hept-5-ene-2-exo-carboxylic acid (1) yielded intermediate 8,9,10-trinorbornene-fused pyrimidinones (5) and hence 3-substituted pyrimidin-4(3 H)-ones (6) through the splitting off of cyclopentadiene. Analogously, the reaction of carboxamides (4) with orthoacetate or orthopropionate led to the formation of 2,3-disubstituted pyrimidin-4(3H)-ones (8). A comparative i.r. and n.m.r. study of compounds (8) and of the previously described derivatives (9) gave unambiguous evidence for the structure of the new compounds. It was also established unequivocally that the products obtained from propiolate with amidines are not the previously assumed 2,3-disubstituted 4(3H)-ones (8), but are in fact the 1,2-disubstituted pyrimidin-4(1H)-ones (9).

Original languageEnglish
Pages (from-to)237-240
Number of pages4
JournalJournal of the Chemical Society, Perkin Transactions 1
Publication statusPublished - 1987

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Pyrimidinones
Amidines
Cyclopentanes
Cyclization
Carboxylic Acids
Derivatives

ASJC Scopus subject areas

  • Chemistry(all)

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title = "Stereochemical studies. Part 103. Saturated heterocycles part 107. Preparation of 3-mono- and 2,3-di-substituted pyrimidin-4(3H)-ones in retro-diels-alder reactions. the correct 1,2-disubstituted structure of the compounds previously described as 2,3-disubstituted derivatives",
abstract = "The orthoformate cyclization of carboxamides (4) obtained from 3-exo-aminobicyclo[2.2.1]hept-5-ene-2-exo-carboxylic acid (1) yielded intermediate 8,9,10-trinorbornene-fused pyrimidinones (5) and hence 3-substituted pyrimidin-4(3 H)-ones (6) through the splitting off of cyclopentadiene. Analogously, the reaction of carboxamides (4) with orthoacetate or orthopropionate led to the formation of 2,3-disubstituted pyrimidin-4(3H)-ones (8). A comparative i.r. and n.m.r. study of compounds (8) and of the previously described derivatives (9) gave unambiguous evidence for the structure of the new compounds. It was also established unequivocally that the products obtained from propiolate with amidines are not the previously assumed 2,3-disubstituted 4(3H)-ones (8), but are in fact the 1,2-disubstituted pyrimidin-4(1H)-ones (9).",
author = "G. St{\'a}jer and Szab{\'o}, {Angela E.} and G. Bern{\'a}th and P. Soh{\'a}r",
year = "1987",
language = "English",
pages = "237--240",
journal = "Journal of the Chemical Society, Perkin Transactions 1",
issn = "1472-7781",
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T1 - Stereochemical studies. Part 103. Saturated heterocycles part 107. Preparation of 3-mono- and 2,3-di-substituted pyrimidin-4(3H)-ones in retro-diels-alder reactions. the correct 1,2-disubstituted structure of the compounds previously described as 2,3-disubstituted derivatives

AU - Stájer, G.

AU - Szabó, Angela E.

AU - Bernáth, G.

AU - Sohár, P.

PY - 1987

Y1 - 1987

N2 - The orthoformate cyclization of carboxamides (4) obtained from 3-exo-aminobicyclo[2.2.1]hept-5-ene-2-exo-carboxylic acid (1) yielded intermediate 8,9,10-trinorbornene-fused pyrimidinones (5) and hence 3-substituted pyrimidin-4(3 H)-ones (6) through the splitting off of cyclopentadiene. Analogously, the reaction of carboxamides (4) with orthoacetate or orthopropionate led to the formation of 2,3-disubstituted pyrimidin-4(3H)-ones (8). A comparative i.r. and n.m.r. study of compounds (8) and of the previously described derivatives (9) gave unambiguous evidence for the structure of the new compounds. It was also established unequivocally that the products obtained from propiolate with amidines are not the previously assumed 2,3-disubstituted 4(3H)-ones (8), but are in fact the 1,2-disubstituted pyrimidin-4(1H)-ones (9).

AB - The orthoformate cyclization of carboxamides (4) obtained from 3-exo-aminobicyclo[2.2.1]hept-5-ene-2-exo-carboxylic acid (1) yielded intermediate 8,9,10-trinorbornene-fused pyrimidinones (5) and hence 3-substituted pyrimidin-4(3 H)-ones (6) through the splitting off of cyclopentadiene. Analogously, the reaction of carboxamides (4) with orthoacetate or orthopropionate led to the formation of 2,3-disubstituted pyrimidin-4(3H)-ones (8). A comparative i.r. and n.m.r. study of compounds (8) and of the previously described derivatives (9) gave unambiguous evidence for the structure of the new compounds. It was also established unequivocally that the products obtained from propiolate with amidines are not the previously assumed 2,3-disubstituted 4(3H)-ones (8), but are in fact the 1,2-disubstituted pyrimidin-4(1H)-ones (9).

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