SYNTHESIS OF PYRAZOLO[4,3-c]QUINOLINES AND THE C-C BOND CLEAVAGE DURING REDUCTIVE CYCLIZATION

被引：3

作者：

Devi, Nisha ^{[1
]}

Gupta, Antriksh ^{[1
]}

Gujjarappa, Raghuram ^{[2
]}

Malakar, Chandi C. ^{[2
]}

Singh, Virender ^{[1
,3
]}

机构：

[1] Dr BR Ambedkar Natl Inst Technol, Dept Chem & Biotechnol, Jalandhar 14401, Punjab, India

[2] Natl Inst Technol Manipur, Dept Chem, Imphal 795004, Manipur, India

[3] Cent Univ Punjab, Dept Chem, Bathinda 151001, Punjab, India

来源：

HETEROCYCLES | 2021年 / 102卷 / 04期

关键词：

BENZODIAZEPINE-RECEPTOR LIGANDS; BAYLIS-HILLMAN ADDUCTS; PYRAZOLE DERIVATIVES; BIOLOGICAL EVALUATION; RECENT PROGRESS; POTENT; ANTIMALARIAL; QUINOLINES; ANTIBACTERIAL; ACTIVATION;

D O I：

10.3987/COM-20-14403

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient synthesis of o-nitrophenyl tethered pyrazole-4-carbaldehydes was achieved via Vilsmeier-Haack formylation of hydrazone derivatives which were subjected to Claisen-Schmidt condensation and Morita-Baylis-Hillman (MBH) reaction with various methyl ketones and activated alkenes respectively to generate the corresponding chalcones and MBH adducts. However, successive Fe-mediated reductive cyclization was followed by an unusual C-C bond cleavage which afforded the pyrazolo[4,3-c]quinolines devoid of diverse substituents at C-4 position.

引用

页码：705 / 722

页数：18

共 77 条

[1]

Abadi AH, 2003, CHEM PHARM BULL, V51, P838

[2] Tri- and Tetrasubstituted Pyrazole Derivates: Regioisomerism Switches Activity from p38MAP Kinase to Important Cancer Kinases [J].

Abu Thaher, Bassam ;

Arnsmann, Martina ;

Totzke, Frank ;

Ehlert, Jan E. ;

Kubbutat, Michael H. G. ;

Schaechtele, Christoph ;

Zimmermann, Markus O. ;

Koch, Pierre ;

Boeckler, Frank M. ;

Laufer, Stefan A. .

JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (02) :961-965

[3] Approaches towards the synthesis of 5-aminopyrazoles [J].

Aggarwal, Ranjana ;

Kumar, Vinod ;

Kumar, Rajiv ;

Singh, Shiv P. .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2011, 7 :179-197

[4] 4-Cyano-5-(2-thiophenyl)-pyrazoles are high affinity CB1 receptor ligands [J].

Altomonte, Stefano ;

Baillie, Gemma L. ;

Ross, Ruth A. ;

Zanda, Matteo .

RSC ADVANCES, 2015, 5 (18) :13692-13701

[5] The pentafluorosulfanyl group in cannabinoid receptor ligands: synthesis and comparison with trifluoromethyl and tert-butyl analogues [J].

Altomonte, Stefano ;

Baillie, Gemma L. ;

Ross, Ruth A. ;

Riley, Jennifer ;

Zanda, Matteo .

RSC ADVANCES, 2014, 4 (39) :20164-20176

[6] New 2-arylpyrazolo[4,3-c]quinoline derivatives as potent and selective human A3 adenosine receptor antagonists [J].

Baraldi, PG ;

Tabrizi, MA ;

Preti, D ;

Bovero, A ;

Fruttarolo, F ;

Romagnoli, R ;

Zaid, NA ;

Moorman, AR ;

Varani, K ;

Borea, PA .

JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (15) :5001-5008

[7] 1,2-Diaryl-1-ethanone and pyrazolo [4,3-c] quinoline-4-one as novel selective cyclooxygenase-2 inhibitors [J].

Baruah, B ;

Dasu, K ;

Vaitilingam, B ;

Vanguri, A ;

Casturi, SR ;

Yeleswarapu, KR .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (02) :445-448

[8] LEPADIFORMINE, A NEW MARINE CYTOTOXIC ALKALOID FROM CLAVELINA-LEPADIFORMIS MULLER [J].

BIARD, JF ;

GUYOT, S ;

ROUSSAKIS, C ;

VERBIST, JF ;

VERCAUTEREN, J ;

WEBER, JF ;

BOUKEF, K .

TETRAHEDRON LETTERS, 1994, 35 (17) :2691-2694

[9] Design and synthesis of hydroxyferroquine derivatives with antimalarial and antiviral activities [J].

Biot, C ;

Daher, W ;

Chavain, N ;

Fandeur, T ;

Khalife, J ;

Dive, D ;

De Clercq, E .

JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (09) :2845-2849

[10] High affinity central benzodiazepine receptor ligands.: Part 3:: Insights into the pharmacophore and pattern recognition study of intrinsic activities of pyrazolo[4,3-c]quinolin-3-ones [J].

Carotti, A ;

Altornare, C ;

Savini, L ;

Chlasserini, L ;

Pellerano, C ;

Mascia, MP ;

Maciocco, E ;

Busonero, F ;

Mameli, M ;

Biggio, G ;

Sanna, E .

BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (23) :5259-5272

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