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
[1]   Intramolecular cyclization of δ-iminoacetylenes:: A new entry to pyrazino[1,2-a]indoles [J].
Abbiati, G ;
Arcadi, A ;
Bellinazzi, A ;
Beccalli, E ;
Rossi, E ;
Zanzola, S .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (10) :4088-4095
[2]   Novel intramolecular cyclization of N-alkynyl heterocycles containing proximate nucleophiles [J].
Abbiati, G ;
Arcadi, A ;
Beccalli, E ;
Rossi, E .
TETRAHEDRON LETTERS, 2003, 44 (28) :5331-5334
[3]  
Abbiati G, 2003, EUR J ORG CHEM, V2003, P1423
[4]  
Abbiati G, 2002, SYNTHESIS-STUTTGART, P1912
[5]  
Abbiati G, 2001, SYNTHESIS-STUTTGART, P2477
[6]   Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes [J].
Alonso, F ;
Beletskaya, IP ;
Yus, M .
CHEMICAL REVIEWS, 2004, 104 (06) :3079-3159
[7]   Synthesis of functionalised quinolines through tandem addition/annulation reactions of β-(2-aminophenyl)-α,β-ynones [J].
Arcadi, A ;
Marinelli, F ;
Rossi, E .
TETRAHEDRON, 1999, 55 (46) :13233-13250
[8]   Pd(II) acts simultaneously as a Lewis acid and as a transition-metal catalyst: Synthesis of cyclic alkenyl ethers from acetylenic aldehydes [J].
Asao, N ;
Nogami, T ;
Takahashi, K ;
Yamamoto, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (05) :764-765
[9]   Cyclisations involving attack of carbo- and heteronucleophiles on carbon-carbon π-bonds activated by organopalladium complexes [J].
Balme, G ;
Bouyssi, D ;
Lomberget, T ;
Monteiro, N .
SYNTHESIS-STUTTGART, 2003, (14) :2115-2134
[10]   Cyclization of carbonyl groups onto alkynes upon reaction with IPy2BF4 and their trapping with nucleophiles:: A versatile trigger for assembling oxygen heterocycles [J].
Barluenga, J ;
Vázquez-Villa, H ;
Ballesteros, A ;
González, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (30) :9028-9029