A retro Diels-Alder method for the preparation of pyrrolo[1,2-a] pyrimidinediones from diexo-aminooxanorbornenecarboxamide

G. Stájer, Angela E. Szabó, P. Sohár, A. Csámpai, Reijo Sillanpää

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

Through the reactions of diexo-3-amino-7-oxanorbornene-2-carboxamide 1 with the oxocarboxylic acids: 4-oxopentanoic acid, p-chlorobenzoylpropionic acid or 2-formylbenzoic acid, the pyrrolo[1,2-a]pyrimidinediones 2 and 3 or pyrimido[1,2-a]isoindoledione 4 were formed on cyclization and thermolysis, when the parent cycles decomposed via the loss of furan to give 2-4 in a retro Diels-Alder reaction. With cis-or trans-2-aroylcyclohexanecarboxylic acids as starting compounds, the 1-aroylhexahydroisoindol-3-ones (5-8) were formed; the phenyl-substituted derivatives gave diastereomeric mixtures. The structures of the new compounds were established by NMR spectroscopy and, for 3 and 6, also by single-crystal X-ray structure determination.

Original languageEnglish
Pages (from-to)239-243
Number of pages5
JournalJournal of Molecular Structure
Volume784
Issue number1-3
DOIs
Publication statusPublished - Feb 20 2006

Fingerprint

preparation
acids
Acids
Thermolysis
Cyclization
Nuclear magnetic resonance spectroscopy
Cycloaddition Reaction
Diels-Alder reactions
Single crystals
furans
Derivatives
X rays
Magnetic Resonance Spectroscopy
X-Rays
nuclear magnetic resonance
cycles
single crystals
spectroscopy
x rays
furan

Keywords

  • Aminooxanorbornenecarboxamide
  • DIFFNOE
  • Isoindolone
  • NMR
  • Pyrrolopyrimidinediones
  • Retro Diels-Alder reaction
  • X-ray

ASJC Scopus subject areas

  • Structural Biology
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Spectroscopy
  • Atomic and Molecular Physics, and Optics
  • Materials Science (miscellaneous)

Cite this

A retro Diels-Alder method for the preparation of pyrrolo[1,2-a] pyrimidinediones from diexo-aminooxanorbornenecarboxamide. / Stájer, G.; Szabó, Angela E.; Sohár, P.; Csámpai, A.; Sillanpää, Reijo.

In: Journal of Molecular Structure, Vol. 784, No. 1-3, 20.02.2006, p. 239-243.

Research output: Contribution to journalArticle

@article{2452114b5f5846749f23d1ef37059da2,
title = "A retro Diels-Alder method for the preparation of pyrrolo[1,2-a] pyrimidinediones from diexo-aminooxanorbornenecarboxamide",
abstract = "Through the reactions of diexo-3-amino-7-oxanorbornene-2-carboxamide 1 with the oxocarboxylic acids: 4-oxopentanoic acid, p-chlorobenzoylpropionic acid or 2-formylbenzoic acid, the pyrrolo[1,2-a]pyrimidinediones 2 and 3 or pyrimido[1,2-a]isoindoledione 4 were formed on cyclization and thermolysis, when the parent cycles decomposed via the loss of furan to give 2-4 in a retro Diels-Alder reaction. With cis-or trans-2-aroylcyclohexanecarboxylic acids as starting compounds, the 1-aroylhexahydroisoindol-3-ones (5-8) were formed; the phenyl-substituted derivatives gave diastereomeric mixtures. The structures of the new compounds were established by NMR spectroscopy and, for 3 and 6, also by single-crystal X-ray structure determination.",
keywords = "Aminooxanorbornenecarboxamide, DIFFNOE, Isoindolone, NMR, Pyrrolopyrimidinediones, Retro Diels-Alder reaction, X-ray",
author = "G. St{\'a}jer and Szab{\'o}, {Angela E.} and P. Soh{\'a}r and A. Cs{\'a}mpai and Reijo Sillanp{\"a}{\"a}",
year = "2006",
month = "2",
day = "20",
doi = "10.1016/j.molstruc.2005.09.011",
language = "English",
volume = "784",
pages = "239--243",
journal = "Journal of Molecular Structure",
issn = "0022-2860",
publisher = "Elsevier",
number = "1-3",

}

TY - JOUR

T1 - A retro Diels-Alder method for the preparation of pyrrolo[1,2-a] pyrimidinediones from diexo-aminooxanorbornenecarboxamide

AU - Stájer, G.

AU - Szabó, Angela E.

AU - Sohár, P.

AU - Csámpai, A.

AU - Sillanpää, Reijo

PY - 2006/2/20

Y1 - 2006/2/20

N2 - Through the reactions of diexo-3-amino-7-oxanorbornene-2-carboxamide 1 with the oxocarboxylic acids: 4-oxopentanoic acid, p-chlorobenzoylpropionic acid or 2-formylbenzoic acid, the pyrrolo[1,2-a]pyrimidinediones 2 and 3 or pyrimido[1,2-a]isoindoledione 4 were formed on cyclization and thermolysis, when the parent cycles decomposed via the loss of furan to give 2-4 in a retro Diels-Alder reaction. With cis-or trans-2-aroylcyclohexanecarboxylic acids as starting compounds, the 1-aroylhexahydroisoindol-3-ones (5-8) were formed; the phenyl-substituted derivatives gave diastereomeric mixtures. The structures of the new compounds were established by NMR spectroscopy and, for 3 and 6, also by single-crystal X-ray structure determination.

AB - Through the reactions of diexo-3-amino-7-oxanorbornene-2-carboxamide 1 with the oxocarboxylic acids: 4-oxopentanoic acid, p-chlorobenzoylpropionic acid or 2-formylbenzoic acid, the pyrrolo[1,2-a]pyrimidinediones 2 and 3 or pyrimido[1,2-a]isoindoledione 4 were formed on cyclization and thermolysis, when the parent cycles decomposed via the loss of furan to give 2-4 in a retro Diels-Alder reaction. With cis-or trans-2-aroylcyclohexanecarboxylic acids as starting compounds, the 1-aroylhexahydroisoindol-3-ones (5-8) were formed; the phenyl-substituted derivatives gave diastereomeric mixtures. The structures of the new compounds were established by NMR spectroscopy and, for 3 and 6, also by single-crystal X-ray structure determination.

KW - Aminooxanorbornenecarboxamide

KW - DIFFNOE

KW - Isoindolone

KW - NMR

KW - Pyrrolopyrimidinediones

KW - Retro Diels-Alder reaction

KW - X-ray

UR - http://www.scopus.com/inward/record.url?scp=33144454379&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33144454379&partnerID=8YFLogxK

U2 - 10.1016/j.molstruc.2005.09.011

DO - 10.1016/j.molstruc.2005.09.011

M3 - Article

AN - SCOPUS:33144454379

VL - 784

SP - 239

EP - 243

JO - Journal of Molecular Structure

JF - Journal of Molecular Structure

SN - 0022-2860

IS - 1-3

ER -