Iodine Catalyzed Highly Efficient One Pot Three Component Synthesis of 4-arylidene-3-methylisoxazol-5 (4H) -one in Aqueous Medium

被引:12
作者
Nakkalwar, Srinivas L. [1 ]
Patwari, Shivaji B. [1 ]
Patel, Mohasim M. [2 ]
Jadhav, Vivekanand B. [2 ]
机构
[1] Lal Bahadur Shastri Coll, Dept Chem, Dharmabad 431809, MH, India
[2] Shri Muktanand Coll, Dept Chem, Gangapur 431109, MH, India
关键词
Aromatic aldehydes containing an electron donating groups; hydroxylamine hydrochloride; ethyl acetoacetate; 4-arylidene-3-methylisoxazol-5(4H)-ones; iodine & water;
D O I
10.2174/2213346105666180711151320
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient one-pot three-component reaction of ethyl acetoacetate with hydroxylamine hydrochloride and various aromatic aldehydes containing an electron donating group, was carried out. The current protocol gives diverse 4-arylidene-3-methylisoxazol-5 (4H) -ones providing good to excellent yield of products in an aqueous medium using iodine as a catalyst. This particular cyclocondensation reaction was performed in water, which is an environmentally benign universal solvent having unique properties being clean, efficient, inexpensive, and readily available.
引用
收藏
页码:121 / 126
页数:6
相关论文
共 71 条
[1]   EFFICIENT ONE-POT SYNTHESIS OF β-UNSATURATED ISOXAZOL-5-ONES AND PYRAZOL-5-ONES UNDER ULTRASONIC IRRADIATION [J].
Ablajan, Keyume ;
Xiamuxi, Hainimu .
SYNTHETIC COMMUNICATIONS, 2012, 42 (08) :1128-1136
[2]   The convenient synthesis of 4-arylmethylidene-4,5-dihydro-3-phenylisoxazol-5-ones [J].
Ablajan, Keyume ;
Xiamuxi, Hainimu .
CHINESE CHEMICAL LETTERS, 2011, 22 (02) :151-154
[3]   The reactivity of 3-methyl-4-nitro-5-styrylisoxazole with some bis-enolisable ketones [J].
Adamo, MFA ;
Chimichi, S ;
De Sio, F ;
Donati, D ;
Sarti-Fantoni, P .
TETRAHEDRON LETTERS, 2002, 43 (23) :4157-4160
[4]   Polymorphic behavior of a yellow isoxazolone dye [J].
Aret, E. ;
Meekes, H. ;
Vlieg, E. ;
Deroover, G. .
DYES AND PIGMENTS, 2007, 72 (03) :339-344
[5]   3-phenyl-4-aroyl-5-isoxazolonate complexes of Tb3+ as promising light-conversion molecular devices [J].
Biju, S. ;
Reddy, M. L. P. ;
Freire, Ricardo O. .
INORGANIC CHEMISTRY COMMUNICATIONS, 2007, 10 (04) :393-396
[6]   SYNTHESIS OF PANTHERINE AND RELATED COMPOUNDS [J].
BOWDEN, K ;
CRANK, G ;
ROSS, WJ .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (02) :172-&
[7]   Organic Synthesis "On Water" [J].
Chanda, Arani ;
Fokin, Valery V. .
CHEMICAL REVIEWS, 2009, 109 (02) :725-748
[8]   An Efficient Synthesis of 4-Arylmethylidene-3-substituted-Isoxazol-5(4H)-ones in Aqueous Medium [J].
Chavan, Abhijit P. ;
Pinjari, Avinash B. ;
Mhaske, Pravin C. .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2015, 52 (06) :1911-1915
[9]  
Cheng QF, 2009, CHINESE J ORG CHEM, V29, P1267
[10]   Recent developments in asymmetric multicomponent reactions [J].
de Graaff, Corien ;
Ruijter, Eelco ;
Orru, Romano V. A. .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (10) :3969-4009