Polyvinylpolypyrrolidone-Supported Chlorosulfonic Acid: An Efficient Catalyst for One-Pot Synthesis of Dihydropyrimidinones and Octahydroquinazolin-2,5-diones

被引：8

作者：

Chegini, Masoumeh Goudarzvand ^{[1
]}

Mokhtary, Masoud ^{[1
]}

机构：

[1] Islamic Azad Univ, Rasht Branch, Dept Chem, POB 3516-41335, Rasht, Iran

来源：

POLYCYCLIC AROMATIC COMPOUNDS | 2017年 / 37卷 / 01期

关键词：

Chlorosulfonic acid; dihydropyrimidinones; octahydroquinazolin-2; 5-diones; polyvinylpolypyrrolidone; solvent-free condition; DERIVATIVES;

D O I：

10.1080/10406638.2015.1088046

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Polyvinylpolypyrrolidone-supported chlorosulfonic acid has been successfully applied to perform one-pot reaction of arylaldehydes, urea, ethylacetoacetate, or cyclic 1,3-diketo compounds under solvent-free condition at 70 degrees C to provide a series of dihydropyrimidinones and octahydroquinazolin-2,5-diones in good to excellent yields. The method offers several advantages such as high yield, short reaction time, simple workup, easy preparation, and reusability of the catalyst. The [PVPP-SO3H]Cl-+(-) catalyst was characterized via Fourier transform infrared spectroscopy (FT-IR) and thermal gravimetric analysis (TGA). Moreover, the catalyst could be recycled several times without significant loss of its catalytic activity. Clean methodologies, easy work-up procedure, high yield, and simple preparation of the catalyst are some advantages of this article.

引用

页码：63 / 72

页数：10

共 31 条

[11] Antagonists of the human adenosine A2A receptor.: Part 3:: Design and synthesis of pyrazolo[3,4-d]pyrimidines, pyrrolo[2,3-d] pyrimidines and 6-arylpurines [J].

Gillespie, Roger J. ;

Cliffe, Ian A. ;

Dawson, Claire E. ;

Dourish, Colin T. ;

Gaur, Suneel ;

Jordan, Allan M. ;

Knight, Antony R. ;

Lerpiniere, Joanne ;

Misra, Anil ;

Pratt, Robert M. ;

Roffey, Jonathan ;

Stratton, Gemma C. ;

Upton, Rebecca ;

Weiss, Scott M. ;

Williamson, Douglas S. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (09) :2924-2929

[12] An efficient one-pot synthesis of octahydroquinazolinone derivatives using catalytic amount of H2SO4 in water [J].

Hassani, Zahra ;

Islami, Mohammad Reza ;

Kalantari, Maryam .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (17) :4479-4482

[13] 12-molybdophosphoric acid: A recyclable catalyst for the synthesis of Biginelli-type 3,4-dihydropyrimidine-2(1H)-ones [J].

Heravi, Majid M. ;

Bakhtiari, Khadijeh ;

Bamoharram, Fatemeh F. .

CATALYSIS COMMUNICATIONS, 2006, 7 (06) :373-376

[14] p-toluenesulfonic acid-catalyzed efficient synthesis of dihydropyrimidines:: Improved high yielding protocol for the Biginelli reaction [J].

Jin, TS ;

Zhang, SL ;

Li, TS .

SYNTHETIC COMMUNICATIONS, 2002, 32 (12) :1847-1851

[15] Ionic liquid: an efficient and recyclable medium for the synthesis of octahydroquinazolinone and biscoumarin derivatives [J].

Khurana, Jitender M. ;

Kumar, Sanjay .

MONATSHEFTE FUR CHEMIE, 2010, 141 (05) :561-564

[16] Synthesis of 4-aryl-7,7-dimethyl-1,2,3,4,5,6,7,8-octahydroquinazoline-2-one/thione-5-one derivatives and evaluation as antibacterials [J].

Kidwai, M ;

Saxena, S ;

Khan, MKR ;

Thukral, SS .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2005, 40 (08) :816-819

[17] CoMFA study, syntheses, antitubercular and anticancer activity of some novel 1,4-dihydropyridines [J].

Kumar, B. R. Prashantha ;

Yuvaraj, S. ;

Srivastava, Anil ;

Chaturvedi, Vanitha ;

Manju, Y. K. ;

Suresh, B. ;

Nanjan, M. J. .

LETTERS IN DRUG DESIGN & DISCOVERY, 2008, 5 (01) :7-14

[18] Multi-step organic synthesis using solid-supported reagents and scavengers: a new paradigm in chemical library generation [J].

Ley, SV ;

Baxendale, IR ;

Bream, RN ;

Jackson, PS ;

Leach, AG ;

Longbottom, DA ;

Nesi, M ;

Scott, JS ;

Storer, RI ;

Taylor, SJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (23) :3815-4195

[19] Nafion-H catalyzed cyclocondensation reaction for the synthesis of octahydroquinazolinone derivatives [J].

Lin, Haixia ;

Zhao, Qingjie ;

Xu, Bin ;

Wang, Xiaohong .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2007, 268 (1-2) :221-226

[20] Microwave-assisted one-pot synthesis of octahydroquinazolinone derivatives using ammonium metavanadate under solvent-free condition [J].

Niralwad, Kirti S. ;

Shingate, Bapurao B. ;

Shingare, Murlidhar S. .

TETRAHEDRON LETTERS, 2010, 51 (28) :3616-3618

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