Fluoride-Assisted Synthesis of 1,4,5,6-Tetrahydropyridazines via [4+2] Cyclodimerization of in Situ-Generated Azoalkenes Followed by a C-N Bond Cleavage

被引：32

作者：

Shelke, Anil M. ^{[1
]}

Suryavanshi, Gurunath ^{[1
]}

机构：

[1] CSIR, Chem Engn & Proc Dev Div, Natl Chem Lab, Dr Homi Bhabha Rd, Pune 411008, Maharashtra, India

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 16期

关键词：

DIELS-ALDER REACTIONS; ELECTRON-POOR 1,2-DIAZA-1,3-DIENES; PROGESTERONE-RECEPTOR LIGANDS; ASYMMETRIC-SYNTHESIS; EFFICIENT SYNTHESIS; (3S)-2,3,4,5-TETRAHYDROPYRIDAZINE-3-CARBOXYLIC ACID; SIMPLE OLEFINS; CYCLOADDITION; DERIVATIVES; TETRAHYDROPYRIDAZINES;

D O I：

10.1021/acs.orglett.6b01551

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An unexpected CsF-assisted C-N bond cleavage was exploited to synthesize highly functionalized and biologically important 1,4,5,6-tetralrydropyridazine derivatives from alpha-halo N-acylhydrazohes in excellent yields. The extrusion of nitrogen and the [4 + 2] cycloaddition between in situ-generated azoalkenes is a key reaction in the process. The identified methodology is suitable for synthesizing a wide variety of analogues of tetrahydropyridazines, which are prevalent in many medicinally important small molecules. The reaction conditions are mild, high-yielding, and amenable for the gram scale.

引用

页码：3968 / 3971

页数：4

共 18 条

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[2] Regioselective Formation of 5-Methylene-6-methoxy-1,4,5,6-tetrahydropyridazines from the [4+2]-Cycloaddition Reaction of In Situ Generated 1,2-Diaza-1,3-dienes with Methoxyallene
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