Metal-Free Conjugate Addition of Alkenylboronic Acids to Enedicarbonyl Compounds towards the Synthesis of Pyridazine Derivatives

被引:5
作者
Roscales, Silvia [1 ]
Sancho, Ainhoa [1 ]
Csaky, Aurelio G. [1 ]
机构
[1] Univ Complutense Madrid, Inst Pluridisciplinar, E-28040 Madrid, Spain
来源
SYNTHESIS-STUTTGART | 2015年 / 47卷 / 15期
关键词
boron; cyclization; isomerization; Michael addition; nucleophilic addition; BOND-FORMING REACTIONS; BORONIC ACIDS; CYCLOADDITION; 1,4-ADDITION; ALKENES; KETONES;
D O I
10.1055/s-0034-1380525
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The regioselective conjugate addition of alkenylboronic acids to electronically-differentiated 1,4-enedicarbonyl compounds under metal-free conditions, using tartaric acid as promoter of the reaction is reported. The resulting compounds have been used as starting materials in the synthesis of 4-alkenyl-4,5-dihydropyridazin-3(2H)-ones or 4-alkylpyridazin-3(2H)-ones by reaction with hydrazine hydrate and acetic acid.
引用
收藏
页码:2233 / 2241
页数:9
相关论文
共 23 条
[1]   Nucleophilicity parameters for designing transition metal-free C-C bond forming reactions of organoboron compounds [J].
Berionni, Guillaume ;
Maji, Biplab ;
Knochel, Paul ;
Mayr, Herbert .
CHEMICAL SCIENCE, 2012, 3 (03) :878-882
[2]  
Berthon-Gelloz G, 2011, BORONIC ACIDS, VOL 2: PREPARATION AND APPLICATIONS IN ORGANIC SYNTHESIS, MEDICINE AND MATERIALS, 2ND EDITION, P263
[3]   Synthesis of Chiral γ-Lactones by One-Pot Sequential Enantioselective Organocatalytic Michael Addition of Boronic Acids and Diastereoselective Intramolecular Passerini Reaction [J].
Bos, Maxence ;
Riguet, Emmanuel .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (22) :10881-10889
[4]   A GENERAL AND STEREOSPECIFIC SYNTHESIS OF TRANS ALKENES AND REGIOSPECIFIC SYNTHESIS OF KETONES VIA STEPWISE HYDROBORATION [J].
BROWN, HC ;
BASAVAIAH, D ;
KULKARNI, SU .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (19) :3808-3810
[5]   VINYLIC ORGANOBORANES .6. A GENERAL-SYNTHESIS OF (E)-DISUBSTITUTED ALKENES OR KETONES VIA THE (E)-(1-SUBSTITUTED-1-ALKENYL)BORONIC ESTERS [J].
BROWN, HC ;
BASAVAIAH, D ;
KULKARNI, SU ;
LEE, HD ;
NEGISHI, E ;
KATZ, JJ .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (26) :5270-5276
[6]   N-Heterocyclic Carbene Catalyzed [4+2] Cycloaddition of Nitroalkenes with Oxodienes [J].
Chen, Xiang-Yu ;
Sun, Li-Hui ;
Ye, Song .
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (14) :4441-4445
[7]   Preparation of Chiral 3-Arylpyrrolidines via the Enantioselective 1,4-Addition of Arylboronic Acids to Fumaric Esters Catalyzed by Rh(I)/Chiral Diene Complexes [J].
Chung, Yu-Chiang ;
Janmanchi, Damodar ;
Wu, Hsyueh-Liang .
ORGANIC LETTERS, 2012, 14 (11) :2766-2769
[8]  
Hall D.G., 2011, BORONIC ACIDS PREPAR, V1, P1
[9]   Rhodium-catalyzed asymmetric 1,4-addition and its related asymmetric reactions [J].
Hayashi, T ;
Yamasaki, K .
CHEMICAL REVIEWS, 2003, 103 (08) :2829-2844
[10]   Iron-Catalyzed Rearrangements and Cycloaddition Reactions of 2H-Chromenes [J].
Luan, Yi ;
Sun, Huan ;
Schaus, Scott E. .
ORGANIC LETTERS, 2011, 13 (24) :6480-6483