Functionalisation of heteroaromatic N-oxides using organic superbase catalyst

被引:42
作者
Araki, Yuta [1 ]
Kobayashi, Koji [1 ]
Yonemoto, Misato [1 ]
Kondo, Yoshinori [1 ]
机构
[1] Tohoku Univ, Grad Sch Pharmaceut Sci, Aoba Ku, Sendai, Miyagi 9808578, Japan
关键词
BASE-INDUCED DEPROTONATION; GRIGNARD-REAGENTS; INTRAMOLECULAR CYCLIZATION; 1-ACYLPYRIDINIUM SALTS; ELECTROPHILIC REACTION; CONVENIENT METHOD; LEAVING GROUP; T-BU-P4; BASE; PYRIDINE; ACTIVATION;
D O I
10.1039/c0ob00740d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Functionalisation of quinoline N-oxide was investigated using phophazene base as a catalyst; alkynylation and heteroarylation at 2-position were successfully achieved via nucleophilic addition-elimination process.
引用
收藏
页码:78 / 80
页数:3
相关论文
共 34 条
[1]  
ALBINI A, 1993, SYNTHESIS-STUTTGART, P263
[2]  
Albini A., 1991, HETEROCYCLIC N OXIDE
[3]   Selective synthesis of 2-substituted pyridine N-oxides via directed ortho-metallation using Grignard reagents [J].
Andersson, Hans ;
Gustafsson, Magnus ;
Olsson, Roger ;
Almqvist, Fredrik .
TETRAHEDRON LETTERS, 2008, 49 (48) :6901-6903
[4]   Synthesis of 2-substituted pyridines via a regiospecific alkylation, alkynylation, and arylation of pyridine N-oxides [J].
Andersson, Hans ;
Almqvist, Fredrik ;
Olsson, Roger .
ORGANIC LETTERS, 2007, 9 (07) :1335-1337
[5]   Reaction of pyridine N-oxides with Grignard reagents:: a stereodefined synthesis of substituted dienal oximes [J].
Andersson, Hans ;
Wang, Xiaoyang ;
Bjorklund, Mikael ;
Olsson, Roger ;
Almqvist, Fredrik .
TETRAHEDRON LETTERS, 2007, 48 (39) :6941-6944
[6]   Palladium-Catalyzed Direct Arylation of Azine and Azole N-Oxides: Reaction Development, Scope and Applications in Synthesis [J].
Campeau, Louis-Charles ;
Stuart, David R. ;
Leclerc, Jean-Philippe ;
Bertrand-Laperle, Megan ;
Villemure, Elisia ;
Sun, Ho-Yan ;
Lasserre, Sandrine ;
Guimond, Nicolas ;
Lecavallier, Melanie ;
Fagnou, Keith .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (09) :3291-3306
[7]   REGIOSELECTIVE ADDITION OF GRIGNARD-REAGENTS TO 1-ACYLPYRIDINIUM SALTS - A CONVENIENT METHOD FOR THE SYNTHESIS OF 4-ALKYL(ARYL)PYRIDINES [J].
COMINS, DL ;
ABDULLAH, AH .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (22) :4315-4319
[8]   ADDITION OF METALLO ENOLATES TO 1-ACYLPYRIDINIUM SALTS - A SHORT SYNTHESIS OF (+/-)-EPI-LUPININE [J].
COMINS, DL ;
BROWN, JD .
TETRAHEDRON LETTERS, 1986, 27 (20) :2219-2222
[9]   Metal-free deprotonative functionalization of heteroaromatics using organic superbase catalyst [J].
Hirono, Yutaro ;
Kobayashi, Koji ;
Yonemoto, Misato ;
Kondo, Yoshinori .
CHEMICAL COMMUNICATIONS, 2010, 46 (40) :7623-7624
[10]   Functionalization of alkynes catalyzed by t-Bu-P4 base [J].
Imahori, T ;
Hori, C ;
Kondo, Y .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) :1090-1092