2,3-heteroaromatic ring-fused cyclohexanones via heteroaromatic homo-Nazarov cyclization of donor-acceptor substituted cyclopropanes

被引:39
作者
Yadav, Veejendra K. [1 ]
Kumar, Naganaboina Vijaya [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India
关键词
D O I
10.1039/b805348k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Heteroaryl 2-silylmethyl-substituted cyclopropyl ketones rearrange under Lewis acid conditions via heteroaromatic homo-Nazarov cyclization to form 2,3-heteroaromatic ring fused 4-t-butyldiphenylsilylmethyl-substituted cyclohexanones.
引用
收藏
页码:3774 / 3776
页数:3
相关论文
共 47 条
[1]   Enantioselective formal synthesis of uleine alkaloids from phenylglycinol-derived bicyclic lactams [J].
Amat, M ;
Pérez, M ;
Llor, N ;
Martinelli, M ;
Molins, E ;
Bosch, J .
CHEMICAL COMMUNICATIONS, 2004, (14) :1602-1603
[2]  
[Anonymous], COMPREHENSIVE ORGANI
[3]   Interrupted nazarov cyclization on silica gel [J].
Dhoro, F ;
Tius, MA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (36) :12472-12473
[4]   SYNTHESIS, BIOLOGICAL IN-VITRO EVALUATION AND STEREOSELECTIVITY OF ONDANSETRON ANALOGS - NOVEL 5-HT2A RECEPTOR ANTAGONISTS [J].
ELZ, S ;
HEIL, WL .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (07) :667-672
[5]  
Fleming I., 1976, FRONTIER ORBITALS OR
[6]   The Nazarov cyclization in organic synthesis. Recent advances [J].
Frontier, AJ ;
Collison, C .
TETRAHEDRON, 2005, 61 (32) :7577-7606
[7]   Unexpected participation of an unconjugated olefin during Nazarov cyclization of bridged bicyclic dienones [J].
Giese, S ;
Mazzola, RD ;
Amann, CM ;
Arif, AM ;
West, FG .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (40) :6546-6549
[8]   SYNTHESIS OF (+/-)-LINDERALACTONE, (+/-)-ISOLINDERALACTONE, AND (+/-)-NEOLINDERALACTONE [J].
GOPALAN, A ;
MAGNUS, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (05) :1756-1757
[9]   STUDIES ON TERPENES .8. TOTAL SYNTHESIS OF (+/-)-LINDERALACTONE, (+--)-ISOLINDERALACTONE, AND (+/-)-NEOLINDERALACTONE, GERMACRANE FURANOSESQUITERPENES [J].
GOPALAN, A ;
MAGNUS, P .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (13) :2317-2321
[10]   Interrupted nazarov reactions using dichlorocyclopropanes: A novel mode of arene trapping [J].
Grant, Tina N. ;
West, F. G. .
ORGANIC LETTERS, 2007, 9 (19) :3789-3792