Green metal-free synthesis of spiro-fused 3,4-pyrazolo[4,3:5,6]pyrido[2,3-d]pyrimidine derivatives via deamination cyclization reactions in aqueous medium

被引:9
作者
Dai, Lei [1 ]
Mao, Kaimin [1 ]
Pan, Zhengbing [1 ]
Rong, Liangce [1 ]
机构
[1] Jiangsu Normal Univ, Sch Chem & Mat Sci, Jiangsu Key Lab Green Synthet Chem Funct Mat, Xuzhou 221116, Jiangsu, Peoples R China
基金
中国国家自然科学基金;
关键词
Pyrazolo[4 ' 3 ':5,6]pyrido[2,3-d] pyrimidine; Green synthesis; Deamination reaction; Aqueous medium; Spiro compound; ONE-POT SYNTHESIS; 3-COMPONENT REACTION; EFFICIENT SYNTHESIS; CATALYST; SPIROOXINDOLE; INHIBITORS; HETEROCYCLES; DISCOVERY; ACID; NANOPARTICLES;
D O I
10.1007/s11164-018-3642-3
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A green metal-free synthesis of spiro-fused 3,4-pyrazolo[4,3:5,6]pyrido[2,3-d]pyrimidine derivatives via deamination cyclization reactions of isatins, substituted 1H-pyrazol-5-amine, and 6-aminopyrimidine-2,4(1H,3H)-dione or 6-amino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione in aqueous medium is reported. This is an efficient route for synthesis of the target products by deamination cyclization reaction. The other advantages of this process are high yield, easy separation, wide substrate range, and environmental friendliness.
引用
收藏
页码:769 / 788
页数:20
相关论文
共 50 条
[41]   Synthesis, characterization and crystal structure of heterocyclic tetrahydropyrido[4′,3′:4,5]thieno[2,3-d]pyrimidinone derivatives via sequential aza-Wittig/base catalyzed cyclization [J].
Chen, Hong ;
Liu, Ming-Guo .
JOURNAL OF MOLECULAR STRUCTURE, 2019, 1180 :31-40
[42]   Convenient Synthesis of New N-3-Substituted Pyrido[1,2:1,5]pyrazolo[3,4-d]pyrimidine-2,4(1H,3H)-dione Derivatives [J].
Belaroussi, Rabia ;
El Bouakher, Abderrahman ;
Marchivie, Mathieu ;
Massip, Stephane ;
Jarry, Christian ;
El Hakmaoui, Ahmed ;
Guillaumet, Gerald ;
Routier, Sylvain ;
Akssira, Mohamed .
SYNTHESIS-STUTTGART, 2013, 45 (18) :2557-2566
[43]   SYNTHESIS AND ANTIMICROBIAL EVALUATION OF SOME NOVEL THIAZOLE, 1,3,4-THIADIAZOLE AND PYRIDO[2,3-d][1,2,4]TRIAZOLO[4,3-a]PYRIMIDINE DERIVATIVES INCORPORATING PYRAZOLE MOIETY [J].
Abdelhamid, Abdou O. ;
Shawali, Ahmad S. ;
Gomha, Sobhi M. ;
El-Enany, Waleed A. M. A. .
HETEROCYCLES, 2015, 91 (11) :2126-2142
[44]   Graphene oxide: a carbocatalyst for the one-pot multicomponent synthesis of 5-aryl-1H-indeno[2′,1′:5,6]pyrido[2,3-d]pyrimidine-2,4,6(3H)-trione [J].
Dehghanpour, Hamid Reza ;
Mosslemin, Mohammad H. ;
Mohebat, Razieh .
JOURNAL OF CHEMICAL RESEARCH, 2018, (01) :35-39
[45]   Synthesis and Biological Evaluation of Fused [1,2,3]Triazolo[4',5':4,5]pyrido[2,3-d]pyrimidine Linked 1,2,3-Triazolesas Potent EGFR Targeting Anticancer Agents [J].
Bandi, Sandhya Rani ;
Reddy, T. Madhukar ;
Janapatla, Uma Rani ;
Narsimha, Sirassu .
RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY, 2023, 49 (SUPPL 1) :S71-S80
[46]   Regioselective Synthesis of New 2,4-(Het)aryl-3H-pyrido[1′,2′:1,5]pyrazolo[4,3-d]pyrimidines Involving Palladium-Catalyzed Cross-Coupling Reactions [J].
Ejjoummany, Abdelaziz ;
Belaroussi, Rabia ;
El Hakmaoui, Ahmed ;
Akssira, Mohamed ;
Guillaumet, Gerald ;
Buron, Frederic ;
Routier, Sylvain .
MOLECULES, 2018, 23 (11)
[47]   Synthesis and dynamic 1H NMR spectroscopic study of 1,4,6,7,8,9-hexahydro-3-methyl-1,4-diphenyl-7-thioxo-5H-pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidin-5-one [J].
Bayat, Mohammad ;
Nasri, Shima ;
Mohammadali, Mohammad Reza .
MONATSHEFTE FUR CHEMIE, 2017, 148 (10) :1833-1842
[48]   Efficient one-pot synthesis of some new pyrimido[5',4':5,6]pyrido[2,3-d]pyrimidines catalyzed by magnetically recyclable Fe3O4 nanoparticles [J].
Fattahi, M. ;
Davoodnia, A. ;
Pordel, M. .
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2017, 87 (04) :863-867
[49]   Efficient one-pot synthesis of some new pyrimido[5′,4′:5,6]pyrido[2,3-d]pyrimidines catalyzed by magnetically recyclable Fe3O4 nanoparticles [J].
M. Fattahi ;
A. Davoodnia ;
M. Pordel .
Russian Journal of General Chemistry, 2017, 87 :863-867
[50]   Facile synthesis of new pyrazolo[4′,3′:5,6]pyrano[2,3-d] pyrimidin-5(1H)-ones via the tandem intramolecular Pinner-Dimroth rearrangement and their antibacterial evaluation [J].
Dorostkar-Ahmadi, Nadieh ;
Davoodnia, Abolghasem ;
Tavakoli-Hoseini, Niloofar ;
Behmadi, Hossein ;
Nakhaei-Moghaddam, Mahboobeh .
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2019, 74 (02) :175-181