First Friedel-Crafts Reaction of the Baylis-Hillman Adducts Derived from Nitroolefins: Application towards Synthesis of Pyrrolidines and Spiropyrrolidines

被引:22
作者
Bakthadoss, Manickam [1 ]
Sivakumar, Nagappan [1 ]
机构
[1] Univ Madras, Dept Organ Chem, Madras 600025, Tamil Nadu, India
关键词
Baylis-Hillman reaction; Friedel-Crafts reaction; intermolecular [3+2] cycloaddition; arylation; spiro compounds; ONE-POT TRANSFORMATION; C-C BONDS; TANDEM CONSTRUCTION; ACETATES; FACILE; PROTOCOL; DESIGN; ENTRY;
D O I
10.1055/s-0030-1260557
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A general and simple protocol for the arylation of Baylis-Hillman adducts derived from nitroolefins leading to novel classes of (E)-2-nitro-1,3-diarylprop-1-enes and 1-[(E)-2-nitro-3-arylallyl]naphthalenes via an intermolecular Friedel-Crafts reaction have been achieved. Further application of these compounds has been demonstrated for the synthesis of pyrrolidines and 3-spiropyrrolidines which are integral components of many natural products and bioactive molecules.
引用
收藏
页码:1296 / 1302
页数:7
相关论文
共 37 条
[1]   Straightforward asymmetric entry to highly functionalized medium-sized rings fused to β-lactams via chemo- and stereocontrolled divergent radical cyclization of Baylis-Hillman adducts derived from 4-oxoazetidine-2-carbaldehydes [J].
Alcaide, B ;
Almendros, P ;
Aragoncillo, C .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (05) :1612-1620
[2]   Highly regio- and stereoselective synthesis of tricyclic frameworks using Baylis-Hillman derivatives [J].
Bakthadoss, Manickain ;
Sivakumar, Nagappan ;
Sivakumar, Govindan ;
Murugan, Gandhi .
TETRAHEDRON LETTERS, 2008, 49 (05) :820-823
[3]   Simple and new protocol for the synthesis of novel (z)-3-arylidenebenzothiazepin-4-ones using Baylis-Hillman derivatives [J].
Bakthadoss, Manickam ;
Murugan, Gandhi .
SYNTHETIC COMMUNICATIONS, 2008, 38 (20) :3406-3413
[4]   Highly Stereoselective Synthesis of Tricyclic Chromenoisoxazolidines by Intramolecular 1,3-Dipolar Cycloadditions [J].
Bakthadoss, Manickam ;
Murugan, Gandhi .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (30) :5825-5830
[5]   Solid-State Melt Reaction for the Domino Process: Highly Efficient Synthesis of Fused Tetracyclic Chromenopyran Pyrimidinediones Using Baylis-Hillman Derivatives [J].
Bakthadoss, Manickam ;
Sivakumar, Govindan ;
Kannan, Damodharan .
ORGANIC LETTERS, 2009, 11 (19) :4466-4469
[6]   Novel Regio- and Stereoselective Synthesis of Functionalized 3-Spiropyrrolidines and 3-Spiropyrrolizidines Using the Baylis-Hillman Adducts Derived from Nitroolefins [J].
Bakthadoss, Manickam ;
Sivakumar, Nagappan .
SYNLETT, 2009, (06) :1014-1018
[7]   Novel Synthesis of (E)-3-Arylidene-2,3-dihydrobenzo[b][1,4]oxazepin-4(5H)-ones Using Baylis-Hillman Derivatives via Reductive Cyclization [J].
Bakthadoss, Manickam ;
Murugan, Gandhi .
SYNTHETIC COMMUNICATIONS, 2009, 39 (07) :1290-1298
[8]   Arylation of the Baylis-Hillman adducts [J].
Basavaiah, D ;
Muthukumaran, K .
TETRAHEDRON, 1998, 54 (19) :4943-4948
[9]  
Basavaiah D, 1996, SYNLETT, P393
[10]   A facile tandem construction of C-O and C-C bonds: a novel one-pot transformation of Baylis-Hillman adducts into 2-benzoxepines [J].
Basavaiah, D ;
Sharada, DS ;
Veerendhar, A .
TETRAHEDRON LETTERS, 2004, 45 (15) :3081-3083