An efficient and improved method for the preparation of nitrites from primary amides and aldoximes

被引：68

作者：

Narsaiah, AV ^{[1
]}

Nagaiah, K ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Fine Chem Lab, Div Organ Chem, Hyderabad 500007, Andhra Pradesh, India

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2004年 / 346卷 / 11期

关键词：

aldoximes; dehydration; nitriles; pivaloyl chloride-pyridine reagent; primary amides;

D O I：

10.1002/adsc.200404059

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The pivaloyl chloride-pyridine system has been utilized as a novel and efficient reagent for the preparation of nitriles from primary amides and aldoximes. The reaction proceeds smoothly under mild reaction conditions and the products are obtained in excellent yields. This method is applicable to a wide range of substrates including aromatic, heterocyclic and aliphatic species. The dehydration takes place at room temperature in the case of primary amides and dichloromethane at reflux temperature is required for rapid conversion in the case of aldoximes.

引用

页码：1271 / 1274

页数：4

共 41 条

[1]

AKBAR S, 1985, SYNTHESIS-STUTTGART, P184

[2]

BAGAR TM, 1980, SYNTHETIC COMMUN, V10, P479

[3] A clean conversion of aldehydes to nitriles using a solid-supported hydrazine [J].

Baxendale, IR ;

Ley, SV ;

Sneddon, HF .

SYNLETT, 2002, (05) :775-777

[4] AlCl3•6H2O/KI/H2O/CH3CN:: A new alternate system for dehydration of oximes and amides in hydrated media [J].

Boruah, M ;

Konwar, D .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (20) :7138-7139

[5] Reagents for organic synthesis: Use of organostannyl oxides as catalytic neutral agents in the preparation of nitriles from primary amides under microwave irradiation [J].

Bose, DS ;

Jayalakshmi, B .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (05) :1713-1714

[6] Aryl chlorothionoformate: A new versatile reagent for the preparation of Nitriles and Isonitriles under mild conditions [J].

Bose, DS ;

Goud, PR .

TETRAHEDRON LETTERS, 1999, 40 (04) :747-748

[7]

Bose DS, 2001, SYNTHESIS-STUTTGART, P373

[8] Efficient one pot synthesis of Nitriles from Aldehydes in solid state using Peroxymonosulfate on Alumina [J].

Bose, DS ;

Narsaiah, AV .

TETRAHEDRON LETTERS, 1998, 39 (36) :6533-6534

[9]

CAMPAGNA F, 1977, TETRAHEDRON LETT, P1813

[10] One-pot synthesis of nitriles from aldehydes under microwave irradiation: Influence of the medium and mode of microwave irradiation on product formation [J].

Chakraborti, AK ;

Kaur, G .

TETRAHEDRON, 1999, 55 (46) :13265-13268

← 1 2 3 4 5 →