Bipyridine carbaldehydes as electrophiles in the Morita-Baylis-Hillman reaction: synthesis of highly functionalized bipyridyl ligands and a macrocycle

被引：8

作者：

Gouthaman, Siddan ^{[1
]}

Periyaraja, Somasundharam ^{[1
]}

Shanmugam, Ponnusamy ^{[1
]}

机构：

[1] CSIR, CLRI, Div Organ Chem, Madras 600020, Tamil Nadu, India

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 43期

关键词：

MBH reaction; Bipyridine; Electrophile; Pyridine-N-oxide; Spiro pyrrolidine oxindole; RUTHENIUM(II); COMPLEXES; ISATIN; ENERGY; ADDUCT;

D O I：

10.1016/j.tetlet.2015.09.032

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and efficient Morita-Baylis-Hillman (MBH) reaction of bipyridine carbaldehydes and unexplored activated alkenes afforded highly functionalized bipyridyl ligands. Particularly, one-pot MBH reaction of 2,2'-bipyridine-4,4'-dicarbaldehyde and 2,2'-bipyridine-4-methyl-4'-carbaldehyde with 1,6-hexanediol diacrylate afforded a twenty membered bipyridyl macrocycle and bis MBH adducts, respectively. Synthetic transformations of mono and bis MBH adducts thus obtained have been demonstrated by preparing bipyridyl N-oxide and [3+2]-cycloadduct of azomethine ylide derived from isatin and proline. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：5920 / 5923

页数：4

共 52 条

[1] Cell survival in a three-dimensional matrix [J].

Alavi, Alireza ;

Stupack, Dwayne G. .

INTEGRINS, 2007, 426 :85-+

[2] Photochemistry and photophysics of Ru(II)-polypyridine complexes in the Bologna group. From early studies to recent developments [J].

Balzani, V ;

Juris, A .

COORDINATION CHEMISTRY REVIEWS, 2001, 211 :97-115

[3] Asymmetric Baylis-Hillman reactions: catalysis using a chiral pyrrolizidine base [J].

Barrett, AGM ;

Cook, AS ;

Kamimura, A .

CHEMICAL COMMUNICATIONS, 1998, (22) :2533-2534

[4] Recent Contributions from the Baylis-Hillman Reaction to Organic Chemistry [J].

Basavaiah, Deevi ;

Reddy, Bhavanam Sekhara ;

Badsara, Satpal Singh .

CHEMICAL REVIEWS, 2010, 110 (09) :5447-5674

[5]

Baylis A. B., 1972, U.S. Patent, Patent No. [3,743,669, 3743669]

[6] Luminescent ruthenium(II) bipyridine-calix[4]arene complexes as receptors for lanthanide cations [J].

Beer, PD ;

Szemes, F ;

Passaniti, P ;

Maestri, M .

INORGANIC CHEMISTRY, 2004, 43 (13) :3965-3975

[7]

Chellappan K., 2005, ANGEW CHEM, V117, P2959

[8] Recent Developments in Top-Emitting Organic Light-Emitting Diodes [J].

Chen, Shufen ;

Deng, Lingling ;

Xie, Jun ;

Peng, Ling ;

Xie, Linghai ;

Fan, Quli ;

Huang, Wei .

ADVANCED MATERIALS, 2010, 22 (46) :5227-5239

[9]

Ciganek E., 1997, ORGANIC REACTIONS, V51, S., P201, DOI [10.1002/0471264180.or051.02, DOI 10.1002/0471264180.OR051.02]

[10] aza-Baylis-Hillman Reaction [J].

Declerck, Valerie ;

Martinez, Jean ;

Lamaty, Frederic .

CHEMICAL REVIEWS, 2009, 109 (01) :1-48

← 1 2 3 4 5 6 →