Department of Chemistry, Faculty of Science; University of Kuwait, Safat, 13060, P.O. Box 5969, Kuwait.
Department of Chemistry, Faculty of Science at Qena, South Valley University, P.O. Box 83523, Qena, Egypt.
Beilstein J Org Chem. 2014 Jan 14;10:141-9. doi: 10.3762/bjoc.10.11.
Novel routes for the preparation of 2-amino-4H-pyran-3-carbonitrile 9, amino-arylbenzoic acid ester derivatives 13a,b, 2-aminotetrahydro-4H-chromene-3-carbonitrile 18, 3-amino-4-cyanotetrahydronaphthalene-2-carboxylic acid ester 26 and 4-amino-3,5-dicyanophthalic acid ester derivatives 37a-c were developed. The synthetic methods utilize one-pot reactions of acetylene carboxylic acid esters, α,β-unsaturated nitriles and/or active methylenenitriles in the presence of L-proline or DABCO. Plausible mechanisms are suggested for the formation of the products. Finally, these compounds were used for the efficient synthesis of 6-amino-5-cyanonicotinic acid ester derivatives 31a,b, ethyl 4-amino-5H-pyrano[2,3-d]pyrimidine-6-carboxylates 33a,b, 4-amino-6H-pyrrolo[3,4-g]quinazoline-9-carbonitrile 39, and 1,7-diamino-6-(N'-hydroxycarbamimidoyl)-3-oxo-5-phenyl-3H-isoindole-4-carboxylate (40).
开发了制备 2-氨基-4H-吡喃-3-甲腈 9、氨基-芳基苯甲酸酯衍生物 13a,b、2-氨基四氢-4H-色烯-3-甲腈 18、3-氨基-4-氰基四氢萘-2-羧酸酯 26 和 4-氨基-3,5-二氰基邻苯二甲酸酯衍生物 37a-c 的新途径。这些合成方法利用脯氨酸或 DABCO 存在下的乙炔羧酸酯、α,β-不饱和腈和/或活性亚甲基腈的一锅反应。提出了形成产物的合理机制。最后，这些化合物被用于高效合成 6-氨基-5-氰基烟酸酯衍生物 31a,b、乙基 4-氨基-5H-吡喃并[2,3-d]嘧啶-6-羧酸酯 33a,b、4-氨基-6H-吡咯并[3,4-g]喹唑啉-9-甲腈 39 和 1,7-二氨基-6-(N'-羟基氨基甲酰基)-3-氧代-5-苯基-3H-异吲哚-4-羧酸酯（40）。
