Solvent-free synthesis of naphthopyrans under ball-milling conditions

被引:87
作者
Dong, Ya-Wei [1 ,2 ]
Wang, Guan-Wu [1 ,2 ]
Wang, Lei [3 ]
机构
[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, Joint Lab Green Synthet Chem, Hefei 230026, Anhui, Peoples R China
[2] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China
[3] Huaibei Coal Teachers Coll, Dept Chem, Huaibei 235000, Anhui, Peoples R China
基金
中国国家自然科学基金;
关键词
Solvent-free; Ball-milling; Propargylic alcohol; Naphthopyran;
D O I
10.1016/j.tet.2008.08.047
中图分类号
O62 [有机化学];
学科分类号
070303 [有机化学]; 081704 [应用化学];
摘要
Under solvent-free ball-milling conditions, the nucleophilic addition reactions of terminal alkynes to carbonyl compounds promoted by KOH proceeded efficiently at ambient temperature. Subsequent cyclization reactions of the synthesized propargylic alcohols with 2-naphthol catalyzed by indium trichloride tetrahydrate, leading to the formation of naphthopyrans, were then investigated. In most cases, side reactions were avoided and thus high yields were achieved. (c) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:10148 / 10154
页数:7
相关论文
共 51 条
[1]
SODIUM DIETHYLDIALKYNYLALUMINATE, A NEW CHEMOSELECTIVE ALKYNYLATING AGENT [J].
AHN, JH ;
JOUNG, MJ ;
YOON, NM .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (19) :6173-6175
[2]
A simple, mild, catalytic, enantioselective addition of terminal acetylenes to aldehydes [J].
Anand, NK ;
Carreira, EM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (39) :9687-9688
[3]
Alkoxide-catalyzed addition of terminal alkynes to ketones [J].
Babler, JH ;
Liptak, VP ;
Phan, N .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (01) :416-417
[4]
Convenient synthesis of linear pyrano[3,2-g]-,[2,3-g]- and angular pyrano[3,2-f]coumarins from 4-[(1,1-dimethyl-2-propynyl)oxy]phenol [J].
Baldoumi, V. ;
Gautam, D. R. ;
Litinas, K. E. ;
Nicolaides, D. N. .
TETRAHEDRON, 2006, 62 (34) :8016-8020
[5]
Mechanically induced solid-state generation of phosphorus ylides and the solvent-free Wittig reaction [J].
Balema, VP ;
Wiench, JW ;
Pruski, M ;
Pecharsky, VK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (22) :6244-6245
[6]
Zeolite-induced heterodomino reaction. Regioselective synthesis of 2H-1-benzopyrans from phenols and alpha-alkynols [J].
Bigi, F ;
Carloni, S ;
Maggi, R ;
Muchetti, C ;
Sartori, G .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (20) :7024-7027
[7]
ORGANOBORANES .38. A FACILE AND HIGHLY EFFICIENT ADDITION OF B-1-ALKYNYL-9-BORABICYCLO[3.3.1]NONANES TO ALDEHYDES AND KETONES - AN EXCEPTIONALLY CHEMOSELECTIVE SYNTHESIS OF PROPARGYLIC ALCOHOLS [J].
BROWN, HC ;
MOLANDER, GA ;
SINGH, SM ;
RACHERLA, US .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (10) :1577-1582
[8]
Synthesis and reactivity of formyl-substituted photochromic 3,3-diphenyl-[3H]-naphtho[2,1-b]pyrans [J].
Chamontin, K ;
Lokshin, V ;
Rossollin, V ;
Samat, A ;
Guglielmetti, R .
TETRAHEDRON, 1999, 55 (18) :5821-5830
[9]
Cheng X, 2005, CHINESE CHEM LETT, V16, P1327
[10]
Acetylenes in catalysis: Enantioselective additions to carbonyl groups and imines and applications beyond [J].
Cozzi, PG ;
Hilgraf, R ;
Zimmermann, N .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (20) :4095-4105