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
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
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DOI：
10.1007/bf00807566
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发表时间：
1997-11-01
影响因子：
1.8
通讯作者：
Palasz, A
中科院分区：
文献类型：
--
作者：
BogdanowiczSzwed, K;Palasz, A
3-芳基-2-苯甲酰基-2-丙烯腈1a-d与烯醇醚2a-c的杂-Diels-桤木反应以79-98%的产率产生2-烷氧基-4，6-二芳基-3，4-二氢-2H-吡喃-5-腈3和4的顺/反非对映异构体。1a-c与环烯醇醚5的类似反应得到具有顺式成环吡喃环的非对映异构体环加合物6和7。3与硫酸反应得到2-羟基-3，4-二氢-2H-吡喃-5-腈8和9。
The hetero-Diels-Alder reaction of 3-aryl-2-benzoyl-2-propenenitriles 1a-d with enol ethers 2a-c yields cis/trans diastereoisomers of 2-alkoxy-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 diastereoisomeric cycloadducts 6 and 7 with cis annulated pyran rings. Reaction of 3 with sulfuric acid leads to 2-hydroxy-3,4-dihydro-2H-pyran-5-carbonitriles 8 and 9.