The Dimroth Rearrangement in the Synthesis of Condensed Pyrimidines - Structural Analogs of Antiviral Compounds

被引:20
作者
Mamedov, Vakhid A. [1 ]
Zhukova, Nataliya A. [1 ]
Kadyrova, Milyausha S. [1 ]
机构
[1] Russian Acad Sci, Kazan Sci Ctr, Arbuzov Inst Organ & Phys Chem, 8 Akad Arbuzova St, Kazan 420088, Russia
关键词
furo[2,3-d]pyrimidines; imidazo[1,2-a]pyrimidines; purines; pyrazolo[3,4-d]pyrimidines; pyrrolo[2,3-d]pyrimidines; quinazolin(on)es; thieno[2,3-d]pyrimidines; 1,2,4]triazolo[1,5-a]pyrimidines; 1,2,4]triazolo[1,5-c]pyrimidines; antiviral activity; Dimroth rearrangement; ONE-POT SYNTHESIS; BIOLOGICAL EVALUATION; FACILE SYNTHESIS; DERIVATIVES; DESIGN; SERIES; INHIBITORS; IDENTIFICATION; CYCLIZATION; VANDETANIB;
D O I
10.1007/s10593-021-02913-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The review discusses the use of the Dimroth rearrangement in the synthesis of condensed pyrimidines which are key structural fragments of antiviral agents. The main attention is given to publications over the past 10 years. The bibliography includes 107 references.
引用
收藏
页码:342 / 368
页数:27
相关论文
共 106 条
[1]   RESEARCH ON HETEROCYCLIC-COMPOUNDS .32. SYNTHESIS AND CYCLOOXYGENASE-INDEPENDENT ANTIINFLAMMATORY AND ANALGESIC ACTIVITY OF IMIDAZO[1,2-A]PYRIMIDINE DERIVATIVES [J].
ABIGNENTE, E ;
SACCHI, A ;
LANERI, S ;
ROSSI, F ;
DAMICO, M ;
BERRINO, L ;
CALDERARO, V ;
PARRILLO, C .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1994, 29 (04) :279-286
[2]   Facile synthesis of novel 6-methyl-5-phenyl-2-sulfido-1,2,3,5-tetrahydro-4H[1,2] oxazolo[4′,5′:5,6]pyrano[2,3-d][1,3,2] diazaphosphinines [J].
Ali, Tarik E. ;
Assiri, Mohamed A. ;
Abdel-Kariem, Somaia M. ;
Yahia, Ibrahim S. .
JOURNAL OF SULFUR CHEMISTRY, 2018, 39 (05) :472-482
[3]  
Anaflous A., 2004, LETT DRUG DES DISCOV, V1, P224, DOI DOI 10.2174/1570180043398885
[4]  
Astakhov A. V., 2012, CHEM HETEROCYC COMPO, V48, P1519
[5]   Synthesis and antiviral study of novel 4-(2-(6-amino-4-oxo-4,5-dihydro-1H-pyrrolo[2,3-d]pyrimidin-3-yl)ethyl)benzamide derivatives [J].
Balaraman, Selvakumar ;
Nayak, Nagaraj ;
Subbiah, Madhuri ;
Elango, Kuppanagounder P. .
MEDICINAL CHEMISTRY RESEARCH, 2018, 27 (11-12) :2538-2546
[6]   Computer-aided identification, synthesis and evaluation of substituted thienopyrimidines as novel inhibitors of HCV replication [J].
Bassetto, Marcella ;
Leyssen, Pieter ;
Neyts, Johan ;
Yerukhimovich, Mark M. ;
Frick, David N. ;
Brancale, Andrea .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2016, 123 :31-47
[7]   Microwave-assisted synthesis of bioactive quinazolines and quinazolinones [J].
Besson, Thierry ;
Chosson, Elizabeth .
COMBINATORIAL CHEMISTRY & HIGH THROUGHPUT SCREENING, 2007, 10 (10) :903-917
[8]   Synthesis of imidazo[1,2-a]pyrazine and imidazo[1,2-a]pyrimidine derivatives [J].
Borisov, A. V. ;
Tolmachev, A. A. ;
Zavada, O. A. ;
Zhuravel', I. A. ;
Kovalenko, S. N. .
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2013, 49 (05) :704-711
[9]   An alternative synthesis of Vandetanib (Caprelsa™) via a microwave accelerated Dimroth rearrangement [J].
Brocklesby, Kayleigh L. ;
Waby, Jennifer S. ;
Cawthorne, Chris ;
Smith, Graham .
TETRAHEDRON LETTERS, 2017, 58 (15) :1467-1469
[10]  
Brown D.J., 1968, MECH MOL MIGRATIONS, V1, P209