An efficient and eco-friendly synthesis of 2-pyridones and functionalized azaxanthone frameworks via indium triflate catalyzed domino reaction

被引：53

作者：

Poomathi, N. ^{[1
,2
]}

Perumal, P. T. ^{[1
]}

Ramakrishna, S. ^{[2
]}

机构：

[1] CSIR Cent Leather Res Inst, Organ Chem Div, Madras 600020, Tamil Nadu, India

[2] Natl Univ Singapore, Ctr Nanofibers & Nanotechnol, Singapore 117576, Singapore

来源：

GREEN CHEMISTRY | 2017年 / 19卷 / 11期

关键词：

BIOLOGICAL EVALUATION; 3-COMPONENT REACTION; ORGANIC-REACTIONS; TOPOISOMERASE-I; INHIBITORS; DERIVATIVES; CYCLOADDITION; ISOCYANATES; DESIGN; POTENT;

D O I：

10.1039/c6gc03440c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A green and efficient one-pot method has been developed for the synthesis of 2-pyridone and functionalized azaxanthone frameworks using indium triflate as an environmentally friendly, reusable catalyst. In this one-pot reaction, 3-formylchromones display a diverse pattern of reactivity upon reaction with different classes of alkenes. An indium triflate-promoted reaction with (Z)-N-methyl-1-(methylthio)-2-nitroethenamine leads to 3-formylchromone annulations to 2-pyridone and analogues via a remarkably facile chromone ring opening. The analogous reaction with N, N'-dimethyl-2-nitroethene-1,1-diamine results in the formation of synthetically useful functionalized azaxanthones via a 6 pi-electrocyclization reaction.

引用

页码：2524 / 2529

页数：6

共 54 条

[1] Oxysporidinone: A novel, antifungal N-methyl-4-hydroxy-2-pyridone from Fusarium oxysporum [J].

Breinholt, J ;

Ludvigsen, S ;

Rassing, BR ;

Rosendahl, CN ;

Nielsen, SE ;

Olsen, CE .

JOURNAL OF NATURAL PRODUCTS, 1997, 60 (01) :33-35

[2] 2-pyridones from cyanoacetamides and enecarbonyl compounds: Application to the synthesis of nothapodytine B [J].

Carles, L ;

Narkunan, K ;

Penlou, S ;

Rousset, L ;

Bouchu, D ;

Ciufolini, MA .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (12) :4304-4308

[3] Recent advances in solventless organic reactions: towards benign synthesis with remarkable versatility [J].

Cave, GWV ;

Raston, CL ;

Scott, JL .

CHEMICAL COMMUNICATIONS, 2001, (21) :2159-2169

[4] Construction of a 3-amino-2-pyridone library by ring-closing metathesis of α-amino acrylamide [J].

Chen, YH ;

Zhang, HJ ;

Nan, FJ .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2004, 6 (05) :684-687

[5] An expeditious, highly efficient, catalyst-free and solvent-free synthesis of nitroamines and nitrosulfides by Michael addition [J].

Choudhary, Garima ;

Peddinti, Rama Krishna .

GREEN CHEMISTRY, 2011, 13 (02) :276-282

[6] Design, synthesis, and biological evaluation of 14-substituted aromathecins as topoisomerase I inhibitors [J].

Cinelli, Maris A. ;

Morrell, Andrew ;

Dexheimer, Thomas S. ;

Scher, Evan S. ;

Pommier, Yves ;

Cushman, Mark .

JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (15) :4609-4619

[7] New bis(pyridyl)methane derivatives from 4-hydroxy-2-pyridones: synthesis and antitumoral activity [J].

Cocco, MT ;

Congiu, C ;

Onnis, V .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2003, 38 (01) :37-47

[8] Synthesis and antitumour activity of 4-hydroxy-2-pyridone derivatives [J].

Cocco, MT ;

Congiu, C ;

Onnis, V .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2000, 35 (05) :545-552

[9] A three-component synthesis of benzochromenodiazocines and chromenopyridines [J].

Dolatkhah, Zahra ;

Nasiri-Aghdam, Mahnaz ;

Bazgir, Ayoob .

TETRAHEDRON LETTERS, 2013, 54 (15) :1960-1962

[10] Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. 8. Pharmacological optimization of orally bioavailable 2-pyridone-containing peptidomimetics [J].

Dragovich, PS ;

Prins, TJ ;

Zhou, R ;

Johnson, TO ;

Hua, Y ;

Luu, HT ;

Sakata, SK ;

Brown, EL ;

Maldonado, FC ;

Tuntland, T ;

Lee, CA ;

Fuhrman, SA ;

Zalman, LS ;

Patick, AK ;

Matthews, DA ;

Wu, EY ;

Guo, M ;

Borer, BC ;

Nayyar, NK ;

Moran, T ;

Chen, LJ ;

Rejto, PA ;

Rose, PW ;

Guzman, MC ;

Dovalsantos, EZ ;

Lee, S ;

McGee, K ;

Mohajeri, M ;

Liese, A ;

Tao, JH ;

Kosa, MB ;

Liu, B ;

Batugo, MR ;

Gleeson, JPR ;

Wu, ZP ;

Liu, J ;

Meador, JW ;

Ferre, RA .

JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (21) :4572-4585

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