Ultrasound-assisted synthesis of pyrimidines and their fused derivatives: A review

被引:23
作者
Mittersteiner, Mateus [1 ]
Farias, Fellipe F. S. [1 ]
Bonacorso, Helio G. [1 ]
Martins, Marcos A. P. [1 ]
Zanatta, Nilo [1 ]
机构
[1] Univ Fed Santa Maria, Dept Quim, Nucleo Quim Heterociclos NUQUIMHE, BR-97105900 Santa Maria, RS, Brazil
关键词
Pyrimidines; Ultrasound; Synergic effects; Heterocycles; Catalysts; ONE-POT SYNTHESIS; ALKOXYVINYL TRIHALOMETHYL KETONES; DIVERSITY-ORIENTED SYNTHESIS; SULFAMIC ACID CATALYSIS; IONIC LIQUID; REGIOSELECTIVE SYNTHESIS; GREEN SYNTHESIS; BIGINELLI REACTION; MULTICOMPONENT SYNTHESIS; 3-COMPONENT SYNTHESIS;
D O I
10.1016/j.ultsonch.2021.105683
中图分类号
O42 [声学];
学科分类号
070206 ; 082403 ;
摘要
The pyrimidine scaffold is present in many bioactive drugs; therefore, efficient synthetic routes that provide shorter reaction times, higher yields, and site-selective reactions are constantly being sought. Ultrasound (US) irradiation has emerged as an alternative energy source in the synthesis of these heterocyclic scaffolds, and over the last ten years there has been a significant increase in the number of publications mentioning US in either the construction or derivatization of the pyrimidine core. This review presents a detailed summary (with 140 ref-erences) of the effects of US (synergic or not) on the construction and derivatization of the pyrimidine core through classical reactions (e.g., multicomponent, cyclocondensation, cycloaddition, and alkylation reactions). The main points that were taken into consideration are as follows: chemo-and regioselectivity issues, and the results of conventional heating methods compared to US and mechanistic insights that are also presented and discussed for key reactions.
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页数:35
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共 270 条
[71]   Vasoactive Thiomethyl-Pyrimidines: Promising Drug Candidates with Vascular Activity [J].
de Andrade, Audrey N. ;
Araujo, Alice V. ;
Barbosa, Hugo B. W. ;
Wanderley, Almir G. ;
Malta, Oscar L. ;
dos Anjos, Janaina V. .
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2017, 28 (07) :1266-1273
[72]   Microwaves in organic synthesis.: Thermal and non-thermal microwave effects [J].
de la Hoz, A ;
Díaz-Ortiz, A ;
Moreno, A .
CHEMICAL SOCIETY REVIEWS, 2005, 34 (02) :164-178
[73]   The Three-Component Biginelli Reaction: A Combined Experimental and Theoretical Mechanistic Investigation [J].
De Souza, Rodrigo O. M. A. ;
da Penha, Eduardo T. ;
Milagre, Humberto M. S. ;
Garden, Simon J. ;
Esteves, Pierre M. ;
Eberlin, Marcos N. ;
Antunes, Octavio A. C. .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (38) :9799-9804
[74]   An easy and fast ultrasonic selective S-alkylation of hetaryl thiols at room temperature [J].
Deligeorgiev, Todor ;
Kaloyanova, Stefka ;
Lesev, Nedyalko ;
Vaquero, Juan J. .
ULTRASONICS SONOCHEMISTRY, 2010, 17 (05) :783-788
[75]   Synthesis of Amido Sulfonamido Heteroaromatics Under Ultrasonication and Their Antimicrobial Activity [J].
Divya, Kuppi Reddy Gari ;
Teja, Gaddam Lakshmi ;
Yamini, Gudi ;
Padmaja, Adivireddy ;
Padmavathi, Venkatapuram .
CHEMISTRY & BIODIVERSITY, 2019, 16 (11)
[76]   Ultrasound-assisted Synthesis of Novel Pyrazole and Pyrimidine Derivatives as Antimicrobial Agents [J].
Dofe, Vidya S. ;
Sarkate, Aniket P. ;
Shaikh, Zarina M. ;
Jadhav, Chetan K. ;
Nipte, Amol S. ;
Gill, Charansingh H. .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2018, 55 (03) :756-762
[77]   Ultrasound-assisted synthesis and antimicrobial activity of tetrazole-based pyrazole and pyrimidine derivatives [J].
Dofe, Vidya S. ;
Sarkate, Aniket P. ;
Shaikh, Zarina M. ;
Gill, Charansingh H. .
HETEROCYCLIC COMMUNICATIONS, 2018, 24 (01) :59-65
[78]   Ultrasound-Mediated Synthesis of Novel 1,2,3-Triazole-Based Pyrazole and Pyrimidine Derivatives as Antimicrobial Agents [J].
Dofe, Vidya S. ;
Sarkate, Aniket P. ;
Shaikh, Zarina M. ;
Gill, Charansingh H. .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 54 (06) :3195-3201
[79]   Chemistry and Biology Of Multicomponent Reactions [J].
Domling, Alexander ;
Wang, Wei ;
Wang, Kan .
CHEMICAL REVIEWS, 2012, 112 (06) :3083-3135
[80]   Highly regioselective synthesis of 7-oxo-7H-[1,3,4]thiadiazolo[3,2-a] pyrimidine-5-carboxylate derivatives under mild conditions [J].
Dong, Hongru ;
Zhao, Yuming .
TETRAHEDRON LETTERS, 2019, 60 (21) :1399-1403