Cycloaddition to 1,3-dialkoxycarbonylallenes: One-step synthesis of heterocyclic compounds containing a dialkyl glutaconate structure.
作者:YASUMITSU TAMURA、TERUHISA TSUGOSHI、SHINICHIRO MOHRI、YUKO NAKAJIMA、YASUYUKI KITA
DOI:10.1248/cpb.33.3257
日期:——
A novel synthesis of alkyl 2-alkoxycarbonyl-3-pyridineacetates (2), alkyl 3-alkoxycarbonyl-4-pyrazoleacetate (5), and alkyl 5-alkoxycarbonyl-4-(1, 2, 3-triazole) acetate (6) is described. Diels-Alder reaction of 1, 3-dialkoxycarbonylallenes (3) with 1-azadiene systems (4) gave 2, and 1, 3-dipolar cycloaddition of 3 to diazoalkanes and trimethylsilylazide gave 5 and 6, respectively. The structures of the cycloadducts and the regiochemistry of the cycloadditions are discussed.
本文描述了 2-烷氧基羰基-3-吡啶乙酸烷基酯 (2)、3-烷氧基羰基-4-吡唑乙酸烷基酯 (5) 和 5-烷氧基羰基-4-(1, 2, 3-三唑)乙酸烷基酯 (6) 的新型合成方法。1,3-二烷氧基羰基烯(3)与 1-氮二烯体系(4)的 Diels-Alder 反应生成了 2,3 与重氮烷烃和三甲基硅烷基氮化物的 1,3-二极环化反应分别生成了 5 和 6。本文讨论了这些环加成产物的结构和环加成反应的反应化学过程。