Sulfated polyborate catalyzed expeditious and efficient three-component synthesis of 3-methyl-4-(hetero)arylmethylene isoxazole-5 (4H)-ones

被引：65

作者：

Patil, Manisha S. ^{[1
]}

Mudaliar, Chirag ^{[1
]}

Chaturbhuj, Ganesh U. ^{[1
]}

机构：

[1] Inst Chem Technol, Dept Pharmaceut Sci & Technol, Mumbai 400019, Maharashtra, India

来源：

TETRAHEDRON LETTERS | 2017年 / 58卷 / 33期

关键词：

Sulfated polyborate; Isoxazole; Aldehyde; Ethyl acetoacetate; Hydroxylamine hydrochloride; ONE-POT SYNTHESIS; AQUEOUS-MEDIA; 3-METHYL-4-ARYLMETHYLENE-ISOXAZOL-5(4H)-ONES; INHIBITORS; MILD; ACID;

D O I：

10.1016/j.tetlet.2017.07.019

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A rapid and highly efficient methodology for the synthesis of 3-methyl-4-(hetero)arylmethylene isoxazole-5(4H)-ones has been developed using sulfated polyborate as a catalyst. The multicomponent reaction of an aromatic/heterocyclic aldehyde, hydroxylamine hydrochloride, and ethyl acetoacetate under a solvent free condition at 80 degrees C is described. This protocol has promising features for the reaction response such as shorter reaction time, easy work-up, ease of separation of pure product with high yields and simplicity in the experimental procedure. The products have been obtained in high yields (80-90%) and convenient reaction time (15-30 min). The method is operationally simple and eco-friendly. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：3256 / 3261

页数：6

共 50 条

[21] An efficient solvent-free synthesis of 3,4-disubstituted isoxazole-5(4H)-ones using microwave irradiation
Kulkarni, Pramod
JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 2021, 98 (01)
[22] One-pot synthesis of 3-methyl-4-arylmethylene-isoxazol-5(4H)-ones
Zhang, Ying-Qun
Ma, Jing-Jun
Wang, Chun
Li, Jing-Ci
Zhang, Dong-Nuan
Zang, Xiao-Huan
Li, Jie
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2008, 28 (01) : 141 - 144
[23] N-bromosuccinimide (NBS)-promoted, three-component synthesis of α,β-unsaturated isoxazol-5(4H)-ones, and spectroscopic investigation and computational study of 3-methyl-4-(thiophen-2-ylmethylene)isoxazol-5(4H)-one
Kiyani, Hamzeh
Kanaani, Ayub
Ajloo, Davood
Ghorbani, Fatemeh
Vakili, Mohammad
RESEARCH ON CHEMICAL INTERMEDIATES, 2015, 41 (10) : 7739 - 7773
[24] Efficient synthesis of isoxazole-5(4H)-ones and polyhydroquinolines using MMWCNTs-PIP and MMWCNTs-MOR
Laeen, Mahdi Behboudi
Pourali, Ali Reza
RESEARCH ON CHEMICAL INTERMEDIATES, 2025, 51 (05) : 2799 - 2827
[25] Sulfated Tin Oxide: A Convenient Heterogeneous Catalyst for the Synthesis of 4-Arylmethylidene-3-Substituted-Isoxazol-5(4H)-Ones
Kaminwar, Nitishkumar S.
Tekale, Sunil. U.
Nakkalwar, Srinivas L.
Pawar, Rajendra P.
LETTERS IN ORGANIC CHEMISTRY, 2021, 18 (12) : 945 - 949
[26] ORGANOCATALYZED THREE-COMPONENT SYNTHESIS OF ISOXAZOL-5(4H)-ONES UNDER AQUEOUS CONDITIONS
Faramarzi, Zeinab
Kiyani, Hamzeh
HETEROCYCLES, 2021, 102 (09) : 1779 - 1790
[27] A catalytic three-component synthesis of isoxazol-5(4H)-ones under green conditions
Gharehassanlou, Sanaz
Kiyani, Hamzeh
INDIAN JOURNAL OF CHEMISTRY, 2022, 61 (05): : 515 - 520
[28] Facile synthesis of 3-methyl-4-arylmethylene-isoxazol-5(4H)-ones catalysed by sodium silicate in an aqueous medium
Liu, Qing
Wu, Ren-Tao
JOURNAL OF CHEMICAL RESEARCH, 2011, (10) : 598 - 599
[29] Green Three-component Synthesis of Merocyanin Dyes Based on 4-Arylideneisoxazol-5(4H)ones
Damghani, Fatemeh K.
Kiyani, Hamzeh
Pourmousavi, Seied A.
CURRENT GREEN CHEMISTRY, 2020, 7 (02) : 217 - 225
[30] A novel dicationic ionic liquid as a highly effectual and dual-functional catalyst for the synthesis of 3-methyl-4-arylmethylene-isoxazole-5(4H)-ones
Irannejad-Gheshlaghchaei, Navid
Zare, Abdolkarim
Sajadikhah, Seyed Sajad
Banaei, Alireza
RESEARCH ON CHEMICAL INTERMEDIATES, 2018, 44 (10) : 6253 - 6266

← 1 2 3 4 5 →