Domino addition/annulation of δ-alkynylaldehydes and oxygen nucleophiles:: a new entry to [1,4]oxazino[4,3-a]indoles

被引:40
作者
Abbiati, G [1 ]
Canevari, V [1 ]
Caimi, S [1 ]
Rossi, E [1 ]
机构
[1] Univ Milan, Fac Farm, Ist Chim Organ Alessandro Marchesini, I-20133 Milan, Italy
关键词
1-alkynyl-1H-indole-2-carbaldehydes; 1,4]oxazino[4,3-a]-indole; domino addition/annulation; alcohol; sodium;
D O I
10.1016/j.tetlet.2005.08.102
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The unusual [1,4]oxazino[4,3-a]indole nucleus was prepared, under mild reaction conditions, by reacting 1-alkynyl-1H-indole-2-carbaldehydes with various alkoxides, generated in situ from the corresponding alkyl, benzyl, allyl and propargyl alcohols. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7117 / 7120
页数:4
相关论文
共 29 条
[11]   DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].
BECKE, AD .
JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652
[12]   Synthesis and intramolecular cyclization of diethylphosphono-substituted allenic glycols [J].
Brel, VK .
SYNTHESIS-STUTTGART, 2001, (10) :1539-1545
[13]   Heterocycles via cyclization of alkynes promoted by organopalladium complexes [J].
Cacchi, S .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 576 (1-2) :42-64
[14]   Synthesis of a heterocyclic aza-enediyne and its DNA-cleavage properties [J].
David, WM ;
Kumar, D ;
Kerwin, SM .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (22) :2509-2512
[15]   Synthesis of alpha,beta-unsaturated aldehydes and methyl carboxylic esters from 2-acetylenic phenyl sulfides. [J].
Fortes, CC ;
Garrote, CFD .
SYNTHETIC COMMUNICATIONS, 1997, 27 (22) :3917-3941
[16]  
HITEMATH SP, 1992, INDIAN J CHEM B, V31, P583
[17]  
JUNG ME, 1991, COMPREHENSIVE ORGANI, V4, P47
[18]   A general and highly regio and stereoselective method for the synthesis of (E)-2-(2-arylvinyl)-3,1-benzoxathiin-4-ones through palladium-copper catalysis [J].
Nandi, B ;
Kundu, NG .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (14) :1649-1655
[19]  
Nikolyukin Y. A., 1994, CHEM HETEROCYCL COMP, V30, P895, DOI [DOI 10.1007/BF01165026, 10.1007/BF01165026]
[20]  
Noguchi M, 1996, TETRAHEDRON, V52, P6581