Ultrasound promoted greener synthesis of spiro[indole-3,5′-[1,3]oxathiolanes in water

被引:37
作者
Dandia, Anshu [1 ]
Singh, Ruby [1 ]
Bhaskaran, Sumit [1 ]
机构
[1] Univ Rajasthan, Dept Chem, Jaipur 302004, Rajasthan, India
关键词
Spiro-oxirane; Water; Sonication; Spiro-oxathiolane; DERIVATIVES; ANALOGS; MEDIA;
D O I
10.1016/j.ultsonch.2009.08.003
中图分类号
O42 [声学];
学科分类号
070206 ; 082403 ;
摘要
An aqueous mediated novel synthesis of substituted 2'amino-4'benzoyl-2'-methyl spiro[indole 3,5'-[1,3]oxathiolane]-2(1H)-ones (2a-f) was carried out from the reaction of spiro [indole-3,2'-oxiranes] (1a-f) with thioacetamide in the presence of LiBr as catalyst. The reaction was carried out under both microwaves and sonication and results were also compared with conventional method. in general, improvement in rate and yields observed when reaction was carried out under sonication as compared to microwave irradiation and conventional method. (C) 2009 Elsevier B.V. All rights reserved.
引用
收藏
页码:399 / 402
页数:4
相关论文
共 53 条
[1]   Synthesis and evaluation of some new spiro indoline-based heterocycles as potentially active antimicrobial agents [J].
Abdel-Rahman, AH ;
Keshk, EM ;
Hanna, MA ;
El-Bady, SM .
BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (09) :2483-2488
[2]   SYNTHESIS AND ANTISECRETORY AND ANTIULCER ACTIVITIES OF DERIVATIVES AND ANALOGS OF 2-(2-PYRIDYL)TETRAHYDROTHIOPHENE-2-CARBOTHIOAMIDE [J].
ALOUP, JC ;
BOUCHAUDON, J ;
FARGE, D ;
JAMES, C ;
DEREGNAUCOURT, J ;
HARDYHOUIS, M .
JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (01) :24-29
[3]   REACTIVITY AND SELECTIVITY IN ORGANIC SONOCHEMICAL REACTIONS INVOLVING INORGANIC SOLIDS [J].
ANDO, T ;
KIMURA, T .
ULTRASONICS, 1990, 28 (05) :326-332
[4]   A green and facile route to γ- and δ-lactones via efficient Pinner-cyclization of hydroxynitriles in water [J].
Aplander, K ;
Hidestål, O ;
Katebzadeh, K ;
Lindström, UM .
GREEN CHEMISTRY, 2006, 8 (01) :22-24
[5]  
BENAHCENE A, 1995, NEW J CHEM, V19, P989
[6]   Recognition of privileged structures by G-protein coupled receptors [J].
Bondensgaard, K ;
Ankersen, M ;
Thogersen, H ;
Hansen, BS ;
Wulff, BS ;
Bywater, RP .
JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (04) :888-899
[7]   Green chemistry - The sonochemical approach [J].
Cintas, P ;
Luche, JL .
GREEN CHEMISTRY, 1999, 1 (03) :115-125
[8]   Power ultrasound in organic systhesis: moving cavitational chemistry from academia to innovative and large-scale applications [J].
Cravotto, G ;
Cintas, P .
CHEMICAL SOCIETY REVIEWS, 2006, 35 (02) :180-196
[9]   The aldol reaction under high-intensity ultrasound: A novel approach to an old reaction [J].
Cravotto, G ;
Demetri, A ;
Nano, GM ;
Palmisano, G ;
Penoni, A ;
Tagliapietra, S .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (22) :4438-4444
[10]   COMMENTS ON THE EVOLVING FIELD OF SONOCHEMISTRY BY A CAVITATION PHYSICIST [J].
CRUM, LA .
ULTRASONICS SONOCHEMISTRY, 1995, 2 (02) :S147-S152