Arylhydrazononitriles as precursors to 2-substituted 1,2,3-triazoles and 4-amino-5-cyano-pyrazole derivatives utilizing microwave and ultrasound irradiation

被引：10

作者：

Al-Zaydi, Khadijah M. ^{[1
]}

Borik, Rita M. ^{[1
]}

Elnagdi, Mohamed H. ^{[2
]}

机构：

[1] King Abdulaziz Univ, Girls Coll Educ, Dept Chem, Jeddah 21533, Saudi Arabia

[2] Kuwait Univ, Dept Chem, Fac Sci, Safat 13060, Kuwait

来源：

GREEN CHEMISTRY LETTERS AND REVIEWS | 2012年 / 5卷 / 03期

关键词：

green synthetic approaches; 2-arylhydrazononitriles; X-ray crystal structure determination; 4-amino-5-cyano-pyrazoles; 1,2,3-triazoles; HETEROCYCLIC SYNTHESIS; ORGANIC-SYNTHESIS; 2-ARYLHYDRAZONONITRILES; ROUTE;

D O I：

10.1080/17518253.2010.483602

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Cyanoacetamides 3a-d were prepared by reacting ethyl cyanoacetate with primary aliphatic amines 2a-d. The formed cyanoacetamides 3a-d were coupled with aromatic diazonium salts to give the corresponding arylhydrazones 4a-i which were used as precursors to title triazoles and pyrazoles by reacting with hydroxylamine and chloroacetonitrile. Yields of products formed by conventional heating are compared with those of microwave and ultrasound irradiation

引用

页码：241 / 250

页数：10

共 28 条

[1] Synthesis and chemical reactivity of 3-oxo-2-arylhydrazono-propanenitriles [J].

Abdallah, SO ;

Metwally, NH ;

Anwar, HF ;

Elnagdi, MH .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2005, 42 (05) :781-786

[2] Studies with 3-functionally substituted 2-arylhydrazononitriles: A new route to 3-substituted-2-arylhydrazononitriles, 4-amino-pyrazole-5-carbonitriles, azadienes and cinnolines [J].

Abdel-Motaleb, Ramadan M. ;

Makhloof, Abdel-Moneim A. ;

Ibrahim, Hamada M. ;

Elnagdi, Mohamed H. .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2006, 43 (04) :931-934

[3] One-pot syntheses of 5-oxo-1,4,5,6,7,8-hexahydroquinolines and pyrimido[4,5-b]quinolines using microwave irradiation and ultrasound [J].

Ahluwalia, VK ;

Goyal, B ;

Das, U .

JOURNAL OF CHEMICAL RESEARCH-S, 1997, (07) :266-&

[4] 2-Arylhydrazononitriles in heterocyclic synthesis:: a novel route to 1,3-diaryl-1,2,4-triazol-5-amines via a Tiemann rearrangement of arylhydrazonoamidoximes [J].

Al-Matar, Hamad M. ;

Riyadh, Sayed M. ;

Elnagdi, Mohamed H. .

ARKIVOC, 2007, :53-62

[5] A microwave assisted diazo coupling reaction: The synthesis of alkylazines and thienopyridazines [J].

Al-Mousawi, Saleh ;

Elassar, Abdel-Zaher ;

El-Apasery, Morsy Ahmed .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2006, 181 (08) :1755-1771

[6] 2-arylhydrazononitriles as building blocks in heterocyclic synthesis:: A novel route to 2-substituted-1,2,3-triazoles and 1,2,3-triazolo[4,5-b]pyridines [J].

Al-Mousawi, Saleh M. ;

Moustafa, Moustafa Sh .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2007, 3

[7]

Al-Saleh B., 2004, J CHEM RES, P580

[8]

Al-Zaydi K. M., 2007, J HETEROCYCLIC CHEM, V44, P1

[9] Microwave assisted condensation reactions of 2-aryl hydrazonopropanals with nucleophilic reagents and dimethyl acetylenedicarboxylate [J].

Al-Zaydi, Khadijah M. ;

Borik, Rita M. .

MOLECULES, 2007, 12 (08) :2061-2079

[10] Studies with arylhydrazonopyridinones: Synthesis of new arylhydrazono thieno[3,4-c]pyridinones as novel D2T2 dye class; classical verse green methodologies [J].

Al-Zaydi, Khadijah M. ;

Borik, Rita M. ;

Elnagdi, Mohamed H. .

ULTRASONICS SONOCHEMISTRY, 2009, 16 (05) :660-668

← 1 2 3 →