A Convenient Synthesis of New Pyrazolo[4,3-d]pyrimidines and Their Fused Heterocycles

被引:12
作者
Rote, Ramhari V. [1 ]
Shelar, Deepak P. [1 ]
Patil, Sandeep R. [1 ]
Jachak, Madhukar N. [1 ]
机构
[1] Univ Pune, KTHM Coll, Organ Chem Res Ctr, Dept Chem, Nasik 422002, Maharashtra, India
关键词
POTENTIAL PURINE ANTAGONISTS; ADENOSINE RECEPTOR ANTAGONISTS; PYRAZOLO-TRIAZOLO-PYRIMIDINE; CROSS-COUPLING REACTION; PYRAZOLO<3,4-D>PYRIMIDINES; 1-ALKENYLBORANES; DERIVATIVES;
D O I
10.1002/jhet.2006
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of some fused heterocycles originated from pyrazolopyrimidines were synthesized using 4-amino1-methyl-3-propyl-1H-pyrazole-5-carboxamide as a starting material. The nucleophilic substitution reactions with different amino acids followed by cyclization and Suzuki-Miyaura cross-coupling reactions with different aryl boronic acids of 7-chloro-5-(4-chlorophenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidine were performed. Also, the oxidative cyclization reactions of 1-(5-(4-chlorophenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7-yl)hydrazine with different aldehydes in the presence of diacetoxy iodobenzene are described. All the synthesized compounds were characterized by analytical and spectroscopic methods.
引用
收藏
页码:815 / 823
页数:9
相关论文
共 50 条
[31]   Synthesis and Antibacterial Evaluation of New Pyrazolo[3,4-d]pyrimidines Kinase Inhibitors [J].
Greco, Chiara ;
Catania, Rosa ;
Balacco, Dario Leonardo ;
Taresco, Vincenzo ;
Musumeci, Francesca ;
Alexander, Cameron ;
Huett, Alan ;
Schenone, Silvia .
MOLECULES, 2020, 25 (22)
[32]   A convenient four-component one-pot strategy toward the synthesis of pyrazolo[3,4-d]pyrimidines [J].
Liu, Mingxing ;
Li, Jiarong ;
Chai, Hongxin ;
Zhang, Kai ;
Yang, Deli ;
Zhang, Qi ;
Shi, Daxin .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2015, 11 :2125-2131
[33]   The Mannich reaction in the synthesis of N,S-containing heterocycles 9. A new approach to thieno[2,3-d]pyrimidines [J].
Dotsenko, V. V. ;
Krivokolysko, S. G. ;
Litvinov, V. P. .
RUSSIAN CHEMICAL BULLETIN, 2009, 58 (07) :1524-1525
[34]   Synthesis and Biological Evaluation of New Chromenes and Chromeno[2,3-d] pyrimidines [J].
Belhadj, Fatima ;
Kibou, Zahira ;
Benabdallah, Mohammed ;
Aissaoui, Mohammed ;
Rahmoun, Mohammed Nadjib ;
Villemin, Didier ;
Choukchou-Braham, Noureddine .
SOUTH AFRICAN JOURNAL OF CHEMISTRY-SUID-AFRIKAANSE TYDSKRIF VIR CHEMIE, 2021, 75 :150-155
[35]   4-Amino-Substituted Pyrazolo[3,4-d]Pyrimidines: Synthesis and Biological Properties [J].
Schenone, S. ;
Bruno, O. ;
Radi, M. ;
Botta, M. .
MINI-REVIEWS IN ORGANIC CHEMISTRY, 2009, 6 (03) :220-233
[36]   Synthesis of Oxazolo[5,4-d][1,2,4]triazolo[4,3-a]pyrimidines as a New Class of Heterocyclic Compounds [J].
Akbarzadeh, Marzieh ;
Bakavoli, Mehdi ;
Eshghi, Hossein ;
Shiri, Ali .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2016, 53 (03) :832-839
[37]   Synthesis of thiazolo[5,4-d][1,2,4]triazolo[4,3-a]pyrimidines as a new class of heterocyclic compounds [J].
Moradi, Hassanali ;
Eshghi, Hossein ;
Bakavoli, Mehdi .
JOURNAL OF CHEMICAL RESEARCH, 2016, (05) :276-279
[38]   Synthesis of 6-hydrazino-3,4-dimethyl-1H-pyrazolo[3,4-d]pyrimidine and its application for the construction of a pyrazolo[4,3-e][1,2,4]triazolo[4,3-a]pyrimidine system [J].
Komkov, A. V. ;
Shashkov, A. S. ;
Baranin, S. V. ;
Dorokhov, V. A. .
RUSSIAN CHEMICAL BULLETIN, 2013, 62 (05) :1248-1254
[39]   Catalyst-free synthesis of benzofuran-fused pyrido [4,3-d]pyrimidines from 2-(2-hydroxyaryl)acetonitrile and 4,6-dichloropyrimidine-5-carbaldehyde through domino condensation reactions [J].
Li, Bo ;
Yue, Zhizhou ;
Xiang, Haoyue ;
Lv, Linlin ;
Song, Shanshan ;
Miao, Zehong ;
Yang, Chunhao .
RSC ADVANCES, 2014, 4 (01) :358-364
[40]   Novel anti-HIV-1 NNRTIs based on a pyrazolo[4,3-d]isoxazole backbone scaffold: design, synthesis and insights into the molecular basis of action [J].
Gomha, Sobhi M. ;
Badrey, Mohamed G. ;
Abdalla, Mohamed M. ;
Arafa, Reem K. .
MEDCHEMCOMM, 2014, 5 (11) :1685-1692