Synthesis of hydrazinoheterocycles from Morita-Baylis-Hillman adducts of nitroalkenes with azodicarboxylates

被引：24

作者：

Mane, Vaijinath ^{[1
]}

Pandey, Jyoti ^{[1
]}

Ayyagari, Narasihmam ^{[1
]}

Dey, Chandan ^{[1
]}

Kale, Raju ^{[1
]}

Namboothiri, Irishi N. N. ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Bombay 400076, Maharashtra, India

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2016年 / 14卷 / 08期

关键词：

POT REGIOSELECTIVE SYNTHESIS; MBH-TYPE REACTION; THIOUREA-TERTIARY AMINE; RAUHUT-CURRIER REACTION; CONJUGATED NITROALKENES; NITROALLYLIC ACETATES; DIASTEREOSELECTIVE SYNTHESIS; TRYPANOCIDAL ACTIVITY; ASYMMETRIC-SYNTHESIS; ANTICANCER ACTIVITY;

D O I：

10.1039/c5ob02656c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Conjugated nitroalkenes and nitrodienes undergo smooth alpha-hydrazination with azodicarboxylates through an imidazole catalyzed carbon-heteroatom bond formation under Morita-Baylis-Hillman conditions. The resulting hydrazinonitroalkenes take part in 1,3-dipolar cycloaddition with azide under mild conditions to give hydrazinotriazoles. A [3 + 2] annulation with phenols and naphthols involving Michael addition and cyclization as the key steps lead to arenodihydrofurans bearing a key hydrazinodicarboxylate moiety. Both regioisomers of naphthodihydrofurans could be synthesized by our methodology by employing the appropriate naphthol.

引用

页码：2427 / 2438

页数：12

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