Diastereoselective synthesis of cis-fused pyrano[4,5-c]pyrrole derivatives via microwave-accelerated intramolecular Knoevenagal hetero Diels-Alder reaction

被引:5
作者
Jayagobi, Mathesan [1 ]
Raghunathan, Raghavachary [1 ]
机构
[1] Univ Madras, Dept Organ Chem, Madras 600025, Tamil Nadu, India
关键词
EFFICIENT SYNTHESIS; SOLVENT-FREE; CYCLOADDITION;
D O I
10.1016/j.tetasy.2010.10.025
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The synthesis of enantiomerically pure pyrano[4 5-c]pyrroles has been accomplished by the intramolecular hetero Diels-Alder reaction of enantiomerically pure N-allyltetheredalkenyl aldehydes with various 1 3-diones The reaction led to the formation of cis-fused enantiomerically pure pyrano[4 5-c]pyrroles in excellent yield under mild conditions and the products were characterized by spectroscopic data (C) 2010 Elsevier Ltd All rights reserved
引用
收藏
页码:2726 / 2732
页数:7
相关论文
共 53 条
[1]   Intramolecular [4+2] cycloadditions of iminoacetonitriles: A new class of azadienophiles for hetero Diels-Alder reactions [J].
Amos, DT ;
Renslo, AR ;
Danheiser, RL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (17) :4970-4971
[2]   Diels-Alder reactions of 1-azadienes [J].
Behforouz, M ;
Ahmadian, M .
TETRAHEDRON, 2000, 56 (30) :5259-5288
[3]   Methodology for regioselective synthesis of substituted pyridines via intramolecular oximino malonate hetero Diels-Alder reactions [J].
Bland, DC ;
Raudenbush, BC ;
Weinreb, SN .
ORGANIC LETTERS, 2000, 2 (25) :4007-4009
[4]  
Boger D.L., 1987, HETERODIELS ALDER ME, P193
[5]  
Boger D.L., 1991, COMPREHENSIVE ORGANI, V5, P451
[6]   Recent developments in imino Diels-Alder reactions [J].
Buonora, P ;
Olsen, JC ;
Oh, T .
TETRAHEDRON, 2001, 57 (29) :6099-6138
[7]  
Carruthers W., 2013, Cycloaddition reactions in organic synthesis
[8]   An approach to total synthesis of the cylindricine B pyridoquinoline subclass of tricyclic marine ascidian alkaloids [J].
Chao, Wenchun ;
Mahajan, Yogesh R. ;
Weinreb, Steven M. .
TETRAHEDRON LETTERS, 2006, 47 (23) :3815-3818
[9]   CHEMICAL AND BIOACTIVE CONSTITUENTS FROM ZANTHOXYLUM SIMULANS [J].
CHEN, IS ;
WU, SJ ;
TSAI, IL ;
WU, TS ;
PEZZUTO, JM ;
LU, MC ;
CHAI, H ;
SUH, N ;
TENG, CM .
JOURNAL OF NATURAL PRODUCTS, 1994, 57 (09) :1206-1211
[10]   cis-1-Ethyl-4,4,6,8-tetramethyl-2-tosyl-2,3,3a,4,6,7,8,9-octahydro-1H-pyrrolo[3′,4′:3,4]pyrano[6,5-d]pyrimidine-7,9-dione [J].
Chinnakali, K. ;
Sudha, D. ;
Jayagobi, M. ;
Raghunathan, R. ;
Fun, Hoong-Kun .
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 :O1862-U3012