Studies on novel synthetic methodologies - Part 74 - An efficient synthesis of 2-benzoxepines from Morita-Baylis-Hillman adducts using heterogeneous recyclable catalysts

被引:13
作者
Das, B [1 ]
Majhi, A [1 ]
Banerjee, J [1 ]
Cowdhury, N [1 ]
Holla, H [1 ]
Harakishore, K [1 ]
Murty, US [1 ]
机构
[1] Indian Inst Chem Technol, Organ Chem Div 1, Hyderabad 500007, Andhra Pradesh, India
关键词
2-benzoxepine; Morita-Baylis-Hillman adduct; formaldehyde; silica supported perchloric acid; Amberlyst-15; anti-bacterial activity;
D O I
10.1248/cpb.54.403
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
2-Benzoxepines have efficiently been synthesized from Morita-Baylis-Hiliman adducts, alkyl 3-aryl-3-hydroxy-2-methylenepropanoates by treatment with HCHO catalyzed by silica supported perchloric acid (HClO4-SiO2)or Amberlyst-15 in CH2Cl2 under reflux for a short period of time (1.5-2.5h). The catalyst can be recovered and recycled. The antibacterial properties of the new 2-benzoxepines were studied but no activity was found.
引用
收藏
页码:403 / 405
页数:3
相关论文
共 21 条
[1]   Mild synthesis of enantiomerically pure imidazo-[1,2-a]azepines mediated by Yb(OTf)3 [J].
Annunziata, R ;
Benaglia, M ;
Raimondi, L .
TETRAHEDRON, 2001, 57 (52) :10357-10363
[2]   A facile tandem construction of C-O and C-C bonds: a novel one-pot transformation of Baylis-Hillman adducts into 2-benzoxepines [J].
Basavaiah, D ;
Sharada, DS ;
Veerendhar, A .
TETRAHEDRON LETTERS, 2004, 45 (15) :3081-3083
[3]   Perchloric acid adsorbed on silica gel as a new, highly efficient, and versatile catalyst for acetylation of phenols, thiols, alcohols, and amines [J].
Chakraborti, AK ;
Gulhane, R .
CHEMICAL COMMUNICATIONS, 2003, (15) :1896-1897
[4]   An efficient stereoselective synthesis of (E)- and (Z)-trisubstituted alkenes from unactivated Baylis-Hillman adducts using NaBH4/CuCl2•2H2O [J].
Das, B ;
Banerjee, J ;
Majhi, A ;
Mahender, G .
TETRAHEDRON LETTERS, 2004, 45 (50) :9225-9227
[5]   A simple and facile stereoselective synthesis of (Z)- and (E)-allyl halides catalyzed by silica supported sodium hydrogen sulfate:: factors influencing the yields and stereochemistry of allyl halides [J].
Das, B ;
Banerjee, J ;
Ravindranath, N .
TETRAHEDRON, 2004, 60 (38) :8357-8361
[6]   Organic reactions in water:: An efficient zinc-mediated stereoselective synthesis of (E)- and (Z)-trisubstituted alkenes using unactivated alkyl halides [J].
Das, B ;
Banerjee, J ;
Mahender, G ;
Majhi, A .
ORGANIC LETTERS, 2004, 6 (19) :3349-3352
[7]   Convenient and efficient stereoselective synthesis of (2Z)-2(chloromethyl)alk-2-enoates using iron(III) or indium(III) chloride [J].
Das, B ;
Banerjee, J ;
Ravindranath, N ;
Venkataiah, B .
TETRAHEDRON LETTERS, 2004, 45 (11) :2425-2426
[8]  
ELKS J, 1990, DICT DRUGS, P1114
[9]  
ELKS J, 1990, DICT DRUGS, P713
[10]  
Elks J., 1990, DICT DRUGS, P984