Zn(OTf)2-Catalyzed Synthesis of 2-Alkynylazetidines and their Ring Expansion to Functionalized 1,4,5,6-Tetrahydropyridines

被引：7

作者：

Shehzadi, Syeda Aaliya ^{[1
]}

Kushwaha, Khushbu ^{[1
]}

Sterckx, Hans ^{[1
]}

Tehrani, Kourosch Abbaspour ^{[1
]}

机构：

[1] Univ Antwerp, Organ Synth, Dept Chem, Groenenborgerlaan 171, B-2020 Antwerp, Belgium

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2018年 / 360卷 / 22期

关键词：

Alkyne; 2-Alkynylazetidine; beta-Chloro imine; Cycloaddition; Ring expansion; Schiff base; Tetrahydropyridine; Zinc; ALLYL DICATION EQUIVALENTS; BICYCLIC SULFAMIDES; TANDEM CYCLIZATION; AZETIDINES; BROMOALLENES; PENARESIDIN; PALLADIUM(0); PYRROLIDINES; ABSENCE; ACID;

D O I：

10.1002/adsc.201800932

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A zinc(II) triflate catalyzed reaction of beta-chloro aldimines with terminal alkynes leading to a rapid and efficient formation of 2-alkynylazetidines in good to excellent yield has been described. The catalytic hydrogenation of the 2-alkynylazetidines resulted in acyclic secondary amines by reductive cleavage of the 2-alkynylazetidine. Further, these non-activated 2-alkynylazetidines were ring expanded in a reaction with dimethyl acetylenedicarboxylate in the presence of zinc(II) triflate to give 4-alkynyltetrahydropyridines. Catalytic reduction of these 4-alkynyltetrahydropyridines led to an efficient conversion to 4-alkyltetrahydropyridine carboxylates.

引用

页码：4393 / 4401

页数：9

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