HETERO-DIELS-ALDER REACTION OF 3-ARYL-2-BENZOYL-2-PROPENENITRILES WITH ENOL ETHERS - SYNTHESIS OF 2-ALKOXY-3,4-DIHYDRO-2H-PYRAN-5-CARBONITRILES

Authors
BOGDANOWICZSZWED K PALASZ A
Citation
K. Bogdanowiczszwed et A. Palasz, HETERO-DIELS-ALDER REACTION OF 3-ARYL-2-BENZOYL-2-PROPENENITRILES WITH ENOL ETHERS - SYNTHESIS OF 2-ALKOXY-3,4-DIHYDRO-2H-PYRAN-5-CARBONITRILES, Monatshefte fuer Chemie, 128(11), 1997, pp. 1157-1172
Citations number
16
Categorie Soggetti
Chemistry
Journal title
Monatshefte fuer Chemie → ACNP
ISSN journal
00269247
Volume
128
Issue
11
Year of publication
1997
Pages
1157 - 1172
Database
ISI
SICI code
0026-9247(1997)128:11<1157:HRO3W>2.0.ZU;2-U
Abstract
The hetero-Diels-Alder reaction of 3-aryl-2-benzoyl-2-propenenitriles 1a-d with enol ethers 2a-c yields cis/trans diastereoisomers of xy-4,6 -diaryl-3,4-dihydro-2H-pyran-5-carbonitriles 3 and 4 in 79-98% yield. The similar reaction of 1a-c with cyclic enol ether 5 affords diastere oisomeric cycloadducts 6 and 7 with cis annulated pyran rings. Reactio n of 3 with sulfuric acid leads to 2-hydroxy-3,4-dihydro-2H-pyran-5-ca rbonitriles 8 and 9.