A Facile One-Pot Synthesis of Chloropyridines from Chalcones

被引:2
作者
Menon, Prasanth K. [1 ,4 ]
Krishnaraj, K. U. [1 ]
George, Sholly C. [1 ,3 ]
Devaky, K. S. [1 ]
Anabha, E. R. [1 ,2 ]
机构
[1] Mahatma Gandhi Univ, Sch Chem Sci, Kottayam 686560, Kerala, India
[2] Sree Narayana Coll, Dept Chem, Alathur 678622, Kerala, India
[3] NIIST, Div Organ Chem, Thiruvananthapuram, Kerala, India
[4] Synthite Ind Ltd, NPD, Cochin 682311, Kerala, India
关键词
ALPHA-FORMYLAROYLKETENE DITHIOACETALS; VILSMEIER-HAACK REACTIONS; CONVENIENT PREPARATION; SUBSTITUTED PYRROLES; CARBONYL-COMPOUNDS; PYRIDINES; 2-AROYL-3,3-BIS(ALKYLSULFANYL)ACRYLALDEHYDES; NAPHTHYRIDINES; CYCLIZATION; REAGENTS;
D O I
10.1002/jhet.1790
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Malononitrile undergoes Michael addition to iminoalkylated chalcones under Vilsmeier-Haack reaction condition. In situ intramolecular cyclization followed by aromatization of the adduct resulted in the formation of 4,6-bis(aryl)-2-chloropyridines in good yields.
引用
收藏
页码:1385 / 1389
页数:5
相关论文
共 33 条
[1]   Synthesis of 3-aroylnicotinonitriles from aroylketene dithioacetals [J].
Anabha, E. R. ;
Nirmala, K. N. ;
Thomas, Abraham ;
Asokan, C. V. .
SYNTHESIS-STUTTGART, 2007, (03) :428-432
[2]   A convenient preparation of 2-aroyl-3,3-bis(alkylsulfanyl)acrylaldehydes and their application in the synthesis of 5-aroyl-2-oxo-1,2-dihydro-2-pyridinecarbonitriles [J].
Anabha, ER ;
Asokan, CV .
SYNTHESIS-STUTTGART, 2006, (01) :151-155
[3]   A facile method for the synthesis of nicotinonitriles from ketones via a one-pot chloromethyleneiminium salt mediated three-component reaction [J].
Asokan, C. V. ;
Anabha, E. R. ;
Thomas, Ajith Dain ;
Jose, Ann Maria ;
Lethesh, K. C. ;
Prasanth, M. ;
Krishanraj, K. U. .
TETRAHEDRON LETTERS, 2007, 48 (32) :5641-5643
[4]  
Balasubramanian M., 1995, PYRIDINE ITS DERI S5, P245
[5]   NEW SYNTHETIC ROUTES TO 3-ARYL-2-CHLOROPYRIDINES, 5-ARYL-2-CHLOROPYRIDINES, AND 6-ARYL-2-CHLOROPYRIDINES [J].
CHURCH, R ;
TRUST, R ;
ALBRIGHT, JD ;
POWELL, DW .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (12) :3750-3758
[6]   Palladium-catalyzed carbonylative coupling of pyridine halides with aryl boronic acids [J].
Couve-Bonnaire, S ;
Carpentier, JF ;
Mortreux, A ;
Castanet, Y .
TETRAHEDRON, 2003, 59 (16) :2793-2799
[7]  
Fallahpour RA, 2000, SYNTHESIS-STUTTGART, P1138
[8]  
Fredericks J.R., 1996, COMPREHENSIVE SUPRAM, P565
[9]   AN ORIGINAL ONE-POT SYNTHESIS OF 5-(4-PYRIDYL)-BENZO[C]-2,7-NAPHTHYRIDINE AS KEY INTERMEDIATE IN THE SYNTHESIS OF AMPHIMEDINE BY METALATION CONNECTED WITH CROSS-COUPLING REACTION [J].
GUILLIER, F ;
NIVOLIERS, F ;
GODARD, A ;
MARSAIS, F ;
QUEGUINER, G .
TETRAHEDRON LETTERS, 1994, 35 (35) :6489-6492
[10]   VILSMEIER-HAACK REACTION WITH GLUTARIMIDES - SYNTHESIS OF 2,6-DICHLORO-1,4-DIHYDROPYRIDINE-3,5-DICARBOXALDEHYDES [J].
GUZMAN, A ;
ROMERO, M ;
MADDOX, ML ;
MUCHOWSKI, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (22) :5793-5797