Hydrazone Radical Promoted Vicinal Difunctionalization of Alkenes and Trifunctionalization of Allyls: Synthesis of Pyrazolines and Tetrahydropyridazines

被引：86

作者：

Duan, Xiao-Yong ^{[1
]}

Yang, Xiu-Long ^{[1
]}

Fang, Ran ^{[1
]}

Peng, Xie-Xue ^{[1
]}

Yu, Wei ^{[1
]}

Han, Bing ^{[1
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 21期

基金：

中国国家自然科学基金;

关键词：

BOND-DISSOCIATION ENTHALPIES; AEROBIC OXIDATIVE SYNTHESIS; METAL-FREE; NITROGEN RADICALS; CYCLIZATION; DIOXYGENATION; DIAMINATION; EFFICIENT; OXIMES; AMIDYL;

D O I：

10.1021/jo4016908

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The intramolecular addition of hydrazone radicals to carbon-carbon double bonds was achieved by using TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy) or DIAD (diisopropyl azodicarboxylate) as the hydrazone radical initiator as well as the carbon radical scavenger. Consequently, alkenes were difunctionalized to afford pyrazolines and tetrahydropyridazines via C-N forming S-exo-trig and 6-exo-trig cyclizations, respectively, and allyls were trifunctionalized to afford pyrazolines via C-N forming tandem 1,5-H-shift/S-exo-trig cyclizations under metal-free neutral conditions.

引用

页码：10692 / 10704

页数：13

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