One-Pot Synthesis of γ-Azidobutyronitriles and Their Intramolecular Cycloadditions

被引：4

作者：

Ivanov, Konstantin L. ^{[1
]}

Tukhtaev, Hamidulla B. ^{[1
]}

Tukhtaeva, Feruza O. ^{[1
]}

Bezzubov, Stanislav I. ^{[2
]}

Melnikov, Mikhail Ya. ^{[1
]}

Budynina, Ekaterina M. ^{[1
,3
]}

机构：

[1] Lomonosov Moscow State Univ, Dept Chem, Leninskie Gory 1-3, Moscow 119991, Russia

[2] Russian Acad Sci, Kurnakov Inst Gen & Inorgan Chem, Leninskiy Pr 31, Moscow 119991, Russia

[3] Russian Acad Sci, Lebedev Phys Inst, Leninskiy Pr 53, Moscow 119991, Russia

来源：

SYNTHESIS-STUTTGART | 2020年 / 52卷 / 22期

基金：

俄罗斯科学基金会;

关键词：

azides; nitriles; one-pot synthesis; 1; 3-dipolar cycloaddition; tetrazoles; Knoevenagel condensation; Corey-Chaykovsky reaction; nucleophilic ring opening; DONOR-ACCEPTOR CYCLOPROPANES; RHAMNO-PYRANOSES; ARYL AZIDES; TETRAZOLES; DERIVATIVES; INHIBITION; ACID; GLYCOSIDES; SCHMIDT; KETONES;

D O I：

10.1055/s-0040-1706402

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Efficient gram-scale, one-pot approaches to azidocyanobutyrates and their amidated or decarboxylated derivatives have been developed, starting from commercially available aldehydes and cyanoacetates. These techniques combine (1) Knoevenagel condensation, (2) Corey-Chaykovsky cyclopropanation and (3) nucleophilic ring opening of donor-acceptor cyclopropanes with the azide ion, as well as (4) Krapcho decarboxylation or (4 ') amidation. The synthetic utility of the resulting gamma-azidonitriles was demonstrated by their transformation into tetrazoles via intramolecular (3+2)-cycloaddition. A condition-dependent activation effect of the alpha-substituent was revealed in that case. Thermally activated azide-nitrile interaction did not differentiate the presence of an alpha-electron-withdrawing substituent in gamma-azidonitriles, whereas the Lewis acid mediated (SnCl(4)or TiCl4) reaction proceeded much easier for azidocyanobutyrates. This allowed us to develop an efficient procedure for converting azidocyanobutyrates into the corresponding tetrazoles.

引用

页码：3356 / 3373

页数：18

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