An optimized procedure for direct access to 1H-indazole-3-carboxaldehyde derivatives by nitrosation of indoles

被引：21

作者：

Chevalier, Arnaud

Ouahrouch, Abdelaaziz

Arnaud, Alexandre

Gallavardin, Thibault ^{[1
]}

Franck, Xavier ^{[1
]}

机构：

[1] Normandie Univ, UNIROUEN, CNRS, INSA Rouen,COBRA,UMR 6014, F-76000 Rouen, France

来源：

RSC ADVANCES | 2018年 / 8卷 / 24期

关键词：

NITROGEN-DIOXIDE; DIAZO-COMPOUNDS; SODIUM-NITRITE; INHIBITORS; DISCOVERY; POTENT; INDAZOLES; KINASE; ACID; EFFICIENT;

D O I：

10.1039/c8ra01546e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Indazole derivatives are currently drawing more and more attention in medicinal chemistry as kinase inhibitors. 1H-indazole-3-carboxaldehydes are key intermediates to access to a variety of polyfunctionalized 3-substituted indazoles. We report here a general access to this motif, based on the nitrosation of indoles in a slightly acidic environment. These very mild conditions allow the conversion of both electron-rich and electron-deficient indoles into 1H-indazole-3-carboxaldehydes.

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页码：13121 / 13128

页数：8

相关论文

共 45 条

[1] Reactions of indoles with nitrogen dioxide and nitrous acid in an aprotic solvent [J].

Astolfi, Paola ;

Panagiotaki, Maria ;

Rizzoli, Corrado ;

Greci, Lucedio .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (17) :3282-3290

[2] ISOLATION AND STRUCTURE DETERMINATION OF NIGELLICINE, A NOVEL ALKALOID FROM THE SEEDS OF NIGELLA-SATIVA [J].

ATTAURRAHMAN ;

MALIK, S ;

HE, CH ;

CLARDY, J .

TETRAHEDRON LETTERS, 1985, 26 (23) :2759-2762

[3] NIGELLIDINE - A NEW INDAZOLE ALKALOID FROM THE SEEDS OF NIGELLA-SATIVA [J].

ATTAURRAHMAN ;

MALIK, S ;

HASAN, SS ;

CHOUDHARY, MI ;

NI, CZ ;

CLARDY, J .

TETRAHEDRON LETTERS, 1995, 36 (12) :1993-1996

[4]

Borchardt A. J., 2004, WO Pat, Patent No. [2004056806A1, 2004056806]

[5] KINETIC-STUDY OF THE NITROSATION OF 3-SUBSTITUTED INDOLES [J].

BRAVO, C ;

HERVES, P ;

LEIS, JR ;

PENA, ME .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1992, (02) :185-189

[6] DIRECT ACTING, HIGHLY MUTAGENIC, ALPHA-HYDROXY N-NITROSAMINES FROM 4-CHLOROINDOLES [J].

BUCHI, G ;

LEE, GCM ;

YANG, D ;

TANNENBAUM, SR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (14) :4115-4119

[7] Convenient method for the 3-functionalization of isoindazoles [J].

Bunnell, A ;

O'Yang, C ;

Petrica, A ;

Soth, MJ .

SYNTHETIC COMMUNICATIONS, 2006, 36 (03) :285-293

[8] CHEMISTRY OF NITROSO-COMPOUNDS .11. NITROSATION OF AMINES BY THE 2-PHASE INTERACTION OF AMINES IN SOLUTION WITH GASEOUS OXIDES OF NITROGEN [J].

CHALLIS, BC ;

KYRTOPOULOS, SA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (02) :299-304

[9] Synthesis and evaluation of heteroaryl-ketone derivatives as a novel class of VEGFR-2 inhibitors [J].

Chekler, Eugene L. Piatnitski ;

Katoch-Rouse, Reeti ;

Kiselyov, Alexander S. ;

Sherman, Dan ;

Ouyang, Xiaohu ;

Kim, Ki ;

Wang, Ying ;

Hadari, Yaron R. ;

Doody, Jacqueline F. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (15) :4344-4347

[10] An efficient large-scale synthesis of 1H-indazole[3-14C]carboxylic acid [J].

Coelho, Richard V., Jr. ;

Schildknegt, Klaas .

JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2007, 50 (7-8) :675-678

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