Poly(N-bromo-N-ethylbenzene-1,3-disulfonamide) and N,N,N′,N′-tetrabromobenzene-1,3-disulfonamide as efficient reagents for synthesis of quinolines

被引:54
作者
Ghorbani-Vaghei, Ramin [1 ]
Akbari-Dadamahaleh, Somayeh [1 ]
机构
[1] Bu Ali Sina Univ, Fac Chem, Dept Organ Chem, Hamadan, Iran
关键词
Quinolines; 2-Aminobenzophenone; Acetylacetone; TBBDA; PBBS; FRIEDLANDER SYNTHESIS; AMINOARYL KETONES; MILD; 1,8-NAPHTHYRIDINES; ANNULATIONS; CATALYST; PROTOCOL; ACID;
D O I
10.1016/j.tetlet.2008.12.076
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Poly(N-bromo-N-ethylbenzene-1,3-disulfonamide) [PBBS] and N,N,N',N'-tetrabromobenzene-1,3-disulfonamide [TBBDA] were used as efficient reagents for the synthesis of quinolines in excellent yields from 2-aminoaryl ketones and carbonyl compounds under aqueous and solvent-free conditions. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1055 / 1058
页数:4
相关论文
共 32 条
[1]   NEW CONJUGATED POLYANTHRAZOLINES CONTAINING THIOPHENE MOIETIES IN THE MAIN CHAIN [J].
AGRAWAL, AK ;
JENEKHE, SA .
MACROMOLECULES, 1991, 24 (25) :6806-6808
[2]   A new green approach to the Friedlander synthesis of quinolines [J].
Arcadi, A ;
Chiarini, M ;
Di Giuseppe, S ;
Marinelli, F .
SYNLETT, 2003, (02) :203-206
[3]   A simple, efficient and solvent-free protocol for the Friedlander synthesis of quinolines by using SnCl2 • 2H2O [J].
Arumugam, P ;
Karthikeyan, G ;
Atchudan, R ;
Muralidharan, D ;
Perumal, PT .
CHEMISTRY LETTERS, 2005, 34 (03) :314-315
[4]   Identification of xanthurenic acid as the putative inducer of malaria development in the mosquito [J].
Billker, O ;
Lindo, V ;
Panico, M ;
Etienne, AE ;
Paxton, T ;
Dell, A ;
Rogers, M ;
Sinden, RE ;
Morris, HR .
NATURE, 1998, 392 (6673) :289-292
[5]   An efficient, high yielding protocol for the synthesis of functionalized quinolines via the tandem addition/annulation reaction of o-aminoaryl ketones with α-methylene ketones [J].
Bose, DS ;
Kumar, RK .
TETRAHEDRON LETTERS, 2006, 47 (05) :813-816
[6]   Synthesis and antibacterial evaluation of certain quinolone derivatives [J].
Chen, YL ;
Fang, KC ;
Sheu, JY ;
Hsu, SL ;
Tzeng, CC .
JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (14) :2374-2377
[7]   A new and efficient one-pot procedure for the synthesis of 2-styrylquinolines [J].
Dabiri, Minoo ;
Salehi, Peyman ;
Baghbanzadeh, Mostafa ;
Nikcheh, Maryam Shakouri .
TETRAHEDRON LETTERS, 2008, 49 (37) :5366-5368
[8]   A mild and efficient one-step synthesis of quinolines [J].
De, SK ;
Gibbs, RA .
TETRAHEDRON LETTERS, 2005, 46 (10) :1647-1649
[9]   Highly regioselective Friedlander annulations with unmodified ketones employing novel amine catalysts: Syntheses of 2-substituted quinolines, 1,8-naphthyridines, and related heterocycles [J].
Dormer, PG ;
Eng, KK ;
Farr, RN ;
Humphrey, GR ;
McWilliams, JC ;
Reider, PJ ;
Sager, JW ;
Volante, RP .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (02) :467-477
[10]   Synthesis of carbocyclic and heterocyclic fused quinolines by cascade radical annulations of unsaturated N-aryl thiocarbamates, thioamides, and thioureas [J].
Du, W ;
Curran, DP .
ORGANIC LETTERS, 2003, 5 (10) :1765-1768