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Synthesis of 3,4-Dihydro-2H-pyrans by Hetero-Diels-Alder Reactions of Functionalized α,β -Unsaturated Carbonyl Compounds with Styrenes

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Synthesis of 3,4-Dihydro-2H-pyrans by Hetero-Diels-Alder Reactions of Functionalized α,β -Unsaturated Carbonyl Compounds with Styrenes

Krystyna Bogdanowicz-Szwed and Aleksandra Pałasz

Department of Organic Chemistry, Jagiellonian University, Ingardena 3, Pl-30060 Krako´w, Poland

Reprint requests to Prof. Dr. K. Bogdanowicz-Szwed. Fax: +48 12 6340515.

E-mail: bogdanow@chemia.uj.edu.pl

Z. Naturforsch.56 b,416Ð422 (2001); received December 12, 2000 Hetero-Diels-AlderReaction,α,β-Unsaturated Ketones, Styrenes

Cycloadditions of 3-aryl-2-benzoyl-2-propenenitriles 1a,bto styrene (2a) and its methyl- or methoxy-substituted derivatives2b-dproceed regio- and diastereoselectively yieldingcis and trans diastereoisomers of 2,4,6-triaryl-3,4-dihydro-2H-pyran-5-carbonitriles 3 and 4 in 59Ð72% yield. Cycloadducts cis-3were the major products. Reaction of 5-(4-nitrobenzyli- dene)-1,3-dimethylbarbituric acid (5) with styrenes2a-dafforded diastereoisomeric mixtures of 2H-pyrano[2,3-d]pyrimidine-2,4(3H)-dionescis-6andtrans-7in 71Ð78% yield.

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