Selective Synthesis of 1-Substituted 4-Chloropyrazolo[3,4-d]pyrimidines

被引：14

作者：

Babu, Suresh ^{[1
]}

Morrill, Christie ^{[1
]}

Almstead, Neil G. ^{[1
]}

Moon, Young-Choon ^{[1
]}

机构：

[1] PTC Therapeut Inc, South Plainfield, NJ 07080 USA

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 08期

关键词：

POTENT; INHIBITORS;

D O I：

10.1021/ol4005382

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Strategies for carrying out the reaction of 4,6-dichloropyrimidine-5-carboxaldehyde with various hydrazines to generate 1-substituted 4-chloropyrazolo[3,4-d]pyrimidines in a selective and high-yielding manner are presented. For aromatic hydrazines, the reaction is performed in the absence of an external base, which promotes exclusive hydrazone formation. The hydrazones subsequently cyclize at an elevated temperature to form the desired pyrazolo[3,4-d]pyrimidine products. For aliphatic hydrazines, the reaction sequence proceeds as a single step in the presence of an external base.

引用

页码：1882 / 1885

页数：4

共 50 条

[1] 4-Amino-Substituted Pyrazolo[3,4-d]Pyrimidines: Synthesis and Biological Properties
Schenone, S.
Bruno, O.
Radi, M.
Botta, M.
MINI-REVIEWS IN ORGANIC CHEMISTRY, 2009, 6 (03) : 220 - 233
[2] Synthesis and in vitro antibacterial evaluation of 6-substituted 4-amino-pyrazolo[3,4-d]pyrimidines
Beyzaei, Hamid
Moghaddam-Manesh, Mohammadreza
Aryan, Reza
Ghasemi, Behzad
Samzadeh-Kermani, Alireza
CHEMICAL PAPERS, 2017, 71 (09) : 1685 - 1691
[3] Synthesis of 4-hydrazinopyrazolo[3,4-d]pyrimidines and their reactions with carbonyl compounds
Edrees, Mastoura M.
JOURNAL OF CHEMICAL RESEARCH, 2013, (01) : 6 - 10
[4] SYNTHESIS OF SUBSTITUTED 4-OXO-3,4-DIHYDRO-THIENO[3,4-d]PYRIMIDINES AND COMPARISON OF THEIR PROPERTIES WITH THOSE OF POSITIONALLY ISOMERIC THIENOPYRIMIDINONES AND BENZO ISOSTERES
Zadorozhny, A. V.
Turov, A. V.
Kovtunenko, V. A.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2010, 46 (08) : 991 - 997
[5] Expanding the scope of fused pyrimidines as kinase inhibitor scaffolds: synthesis and modification of pyrido[3,4-d]pyrimidines
Innocenti, Paolo
Woodward, Hannah
O'Fee, Lisa
Hoelder, Swen
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (03) : 893 - 904
[6] Recent green approaches for the synthesis of pyrazolo[3,4-d]pyrimidines: A mini review
Maher, Mai
Zaher, Ashraf F.
Mahmoud, Zeinab
Kassab, Asmaa E.
ARCHIV DER PHARMAZIE, 2022, 355 (06)
[7] Design, synthesis and cytotoxic activity of some novel compounds containing pyrazolo[3,4-d]pyrimidines nucleus
Kandeel, Manal M.
Roshdy, Sameha M.
Abdelall, Eman K. A.
Abdelgawad, Mohamed A.
Lamie, Phoebe F.
JOURNAL OF CHEMICAL SCIENCES, 2013, 125 (05) : 1029 - 1043
[8] Design and Synthesis of Novel Pyrazolo[3,4-d]Pyrimidines:In VitroCytotoxic Evaluation and Free Radical Scavenging Activity Studies
Alharthy, Rima D.
PHARMACEUTICAL CHEMISTRY JOURNAL, 2020, 54 (03) : 273 - 278
[9] An alternative synthetic approach for the synthesis of biologically relevant 1,4-disubstituted pyrazolo[3,4-d]pyrimidines
Radi, Marco
Bernardo, Vincenzo
Vignaroli, Giulia
Brai, Annalaura
Biava, Mariangela
Schenone, Silvia
Botta, Maurizio
TETRAHEDRON LETTERS, 2013, 54 (38) : 5204 - 5206
[10] Microwave-assisted synthesis of N1-and C3-substituted pyrazolo[3,4-d]pyrimidine libraries
Todorovic, Nick
Awuah, Emelia
Shakya, Tushar
Wright, Gerard D.
Capretta, Alfredo
TETRAHEDRON LETTERS, 2011, 52 (44) : 5761 - 5763

← 1 2 3 4 5 →