Zirconocene dichloride catalyzed multi-component synthesis of 1-amidoalkyl-2-naphthols at ambient temperature

被引：16

作者：

Khanapure, Sharanabasappa ^{[1
]}

Jagadale, Megha ^{[1
]}

Salunkhe, Rajashri ^{[1
]}

Rashinkar, Gajanan ^{[1
]}

机构：

[1] Shivaji Univ, Dept Chem, Kolhapur 416004, Maharashtra, India

来源：

RESEARCH ON CHEMICAL INTERMEDIATES | 2016年 / 42卷 / 03期

关键词：

Multi-component reaction; Zirconocene dichloride; 1-Amidoalkyl-2-naphthols; o-Quinine methide; ONE-POT SYNTHESIS; AMIDOALKYL NAPHTHOLS; EFFICIENT SYNTHESIS; IONIC LIQUID; ORGANIC-SYNTHESIS; RAPID SYNTHESIS; HYDROZIRCONATION; POLYMERIZATION; MILD; ORGANOZIRCONIUM;

D O I：

10.1007/s11164-015-2136-9

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Zirconocene dichloride (Cp2ZrCl2) was found to be highly efficient catalyst for the synthesis of structurally diverse 1-amidoalkyl-2-naphthols by one-pot multi-component reaction (MCR) of 2-naphthol with a variety of aryl aldehydes and amides under ambient temperature. The activation of both carbonyl groups of aryl aldehydes and the o-quinine methide intermediate accounts for the high reactivity of Cp2ZrCl2. [GRAPHICS] .

引用

页码：2075 / 2085

页数：11

共 57 条

[1] Synthesis of 1-amidoalkyl-2-naphthols and oxazine derivatives with study of their antibacterial and antiviral activities [J].

Abou-Elmagd, Wael S. I. ;

Hashem, Ahmed I. .

MEDICINAL CHEMISTRY RESEARCH, 2013, 22 (04) :2005-2013

[2] HYDROZIRCONATION .5. GAMMA,DELTA-UNSATURATED ALDEHYDES AND HALIDES FROM 1,3-DIENES VIA ORGANOZIRCONIUM(IV) INTERMEDIATES [J].

BERTELO, CA ;

SCHWARTZ, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (01) :262-264

[3] Cp2ZrCl2-induced Reformatsky and Barbier reactions on isatins: an efficient synthesis of 3-substituted-3-hydroxyindolin-2-ones [J].

Chouhan, Mangilal ;

Sharma, Ratnesh ;

Nair, Vipin A. .

APPLIED ORGANOMETALLIC CHEMISTRY, 2011, 25 (06) :470-475

[4] Perchloric acid-silica (HClO4•SiO2)-catalyzed synthesis of 14-alkyl- or 14-aryl-14H-dibenzo[a,j]xanthenes and N-[(2-hydroxynaphthalen-1-yl)methyl]amides [J].

Das, Biswanath ;

Kumar, D. Nandan ;

Laxminarayana, Keetha ;

Ravikanth, B. .

HELVETICA CHIMICA ACTA, 2007, 90 (07) :1330-1334

[5] Iodine catalyzed preparation of amidoalkyl naphthols in solution and under solvent-free conditions [J].

Das, Biswanath ;

Laxminarayana, Keetha ;

Ravikanth, B. ;

Rao, B. Rama .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2007, 261 (02) :180-183

[6] Piper-Betle-Shaped Nano-S-Catalyzed Synthesis of 1-Amidoalkyl-2-naphthols under Solvent-Free Reaction Condition: A Greener "Nanoparticle-Catalyzed Organic Synthesis Enhancement" Approach [J].

Das, Vijay K. ;

Borah, Madhurjya ;

Thakur, Ashim J. .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (07) :3361-3366

[7]

Davies A. G., 2000, LEWIS ACIDS ORGANIC

[8] IONIC LIQUID [NMP]+HSO4-: AN EFFICIENT AND RECYCLABLE CATALYST FOR THE SYNTHESIS OF 1-AMIDOALKYL-2-NAPHTHOLS AND 1-CARBAMATOALKYL-2-NAPHTHOLS UNDER SOLVENT-FREE CONDITIONS [J].

Deshmukh, Krishna M. ;

Qureshi, Ziyauddin S. ;

Patil, Yogesh P. ;

Bhanage, Bhalchandra M. .

SYNTHETIC COMMUNICATIONS, 2012, 42 (01) :93-101

[9] H3Mo12O40P-Catalyzed One-Pot Synthesis of Amidoalkyl Naphthols [J].

Gawand, Preeti ;

Deokar, Hrushikesh ;

Langi, Bhushan ;

Yadav, Arun ;

Chaskar, Atul .

SYNTHETIC COMMUNICATIONS, 2009, 39 (23) :4171-4179

[10] HYDROZIRCONATION ORGANIC SYNTHESIS VIA ORGANOZIRCONIUM INTERMEDIATES - SYNTHESIS AND REARRANGEMENT OF ALKYLZIRCONIUM(IV) COMPLEXES AND THEIR REACTION WITH ELECTROPHILES [J].

HART, DW ;

SCHWARTZ, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (26) :8115-8116

← 1 2 3 4 5 6 →