A simplified green chemistry approaches to synthesis of 2-substituted 1,2,3-triazoles and 4-amino-5-cyanopyrazole derivatives conventional heating versus microwave and ultrasound as ecofriendly energy sources

被引:25
作者
Al-Zaydi, Khadijah M. [1 ]
机构
[1] King Abdulaziz Univ, Dept Chem, Girls Coll Educ, Jeddah 21533, Saudi Arabia
关键词
Ecofriendly energy sources; Green chemistry; 2-Arylhydrazonocyano acetamides; 1,2,3-Triazole; Triazolopyrimidine; Pyrazol-4-amine; Microwave irradiation; Ultrasound irradiation; HETEROCYCLIC SYNTHESIS; 2-ARYLHYDRAZONONITRILES; ROUTE; PRECURSORS; REAGENTS;
D O I
10.1016/j.ultsonch.2009.02.007
中图分类号
O42 [声学];
学科分类号
070206 ; 082403 ;
摘要
Cyanoacetamides 3 were prepared via reacting ethyl cyanoacetate with benzylamine. Yields and reaction times needed for reaction completion at room temperature, by microwaves (mu omega) heating and under ultrasound (US) irradiations are compared. The formed cyanoacetamides were coupled with aromatic diazonium salts and the formed arylhydrazones were used as precursors to title triazoles and pyrazoles via reacting the former with hydroxylamine and chloroacetonitrile. Yields of products formed via conventional heating are compared with those of mu omega and US irradiation. (C) 2009 Elsevier B.V. All rights reserved.
引用
收藏
页码:805 / 809
页数:5
相关论文
共 24 条
[1]   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
[2]   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
[3]   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
[4]   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
[5]  
Al-Saleh B, 2004, J CHEM RES, P578
[6]   Studies with enaminones: Formation of a N,O-cyclicacetal on coupling of 3-dimethylamino-1-hydroxyphenyl-2-propenone with arenediazonium salts [J].
Al-Zaydi, Khadijah M. ;
Borik, Rita M. ;
Elnagdi, Mohamed H. .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2007, 44 (05) :1187-1189
[7]   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
[8]  
ALZAYDI KM, 2003, MOLECULES, V8, P910
[9]  
ALZAYDI KM, ULTRASONICS IN PRESS
[10]  
Anwar HF, 2005, J CHEM RES, P29