An efficient one-pot multi-component synthesis of highly functionalized piperidines

被引:17
作者
Goswami, Santosh V. [1 ]
Thorat, Prashant B. [1 ]
Bhusare, Sudhakar R. [1 ]
机构
[1] Dnyanopasak Coll, Dept Chem, Parbhani 431401, Maharashtra, India
关键词
aniline; aromatic aldehyde; 1,3-dicarbonyl compound; phenylboronic acid; piperidines; PHENYLBORONIC ACID; CONCISE SYNTHESIS; 1,4-DIHYDROPYRIDINES; CYCLIZATION; POSITION; ATOM;
D O I
10.1515/hc-2012-0105
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple, inexpensive and efficient one-pot synthesis of piperidine derivatives was achieved in excellent yield via the three-component reaction of substituted aniline, 1,3-dicarbonyl compound and aromatic aldehyde using phenylboronic acid as catalyst.
引用
收藏
页码:245 / 248
页数:4
相关论文
共 25 条
[1]   3-Nitrophenylboronic acid-catalyzed efficient one-pot synthesis of 1,4-dihydropyridines and polyhydroquinolines [J].
Adude, Ramkishan N. ;
Tigote, Ramkishan M. ;
Goswami, Santosh V. ;
Bhusare, Sudhakar R. .
INTERNATIONAL JOURNAL OF INDUSTRIAL CHEMISTRY, 2012, 3 (01) :1-3
[2]   Iron(III)-promoted aza-prins-cyclization:: Direct synthesis of six-membered azacycles [J].
Carballo, Ruben M. ;
Ramirez, Miguel A. ;
Rodriguez, Matias L. ;
Martin, Victor S. ;
Padron, Juan I. .
ORGANIC LETTERS, 2006, 8 (17) :3837-3840
[3]   Pot, atom and step economic (PASE) synthesis of highly functionalized piperidines: a five-component condensation [J].
Clarke, Paul A. ;
Zaytzev, Andrey V. ;
Whtwoo, Adrian C. .
TETRAHEDRON LETTERS, 2007, 48 (30) :5209-5212
[4]   Alkaloids from amphibian skin: A tabulation of over eight-hundred compounds [J].
Daly, JW ;
Spande, TF ;
Garraffo, HM .
JOURNAL OF NATURAL PRODUCTS, 2005, 68 (10) :1556-1575
[5]   Intramolecular Mannich reaction in the asymmetric synthesis of polysubstituted piperidines: Concise synthesis of the dendrobate alkaloid (+)-241D and its C-4 epimer [J].
Davis, FA ;
Chao, B ;
Rao, A .
ORGANIC LETTERS, 2001, 3 (20) :3169-3171
[6]   One-pot synthesis of 1,4-dihydropyridines via a phenylboronic acid catalyzed Hantzsch three-component reaction [J].
Debache, Abdelimadjid ;
Boulcina, Raouf ;
Belfaitah, Ali ;
Rhouati, Salah ;
Carboni, Bertrand .
SYNLETT, 2008, (04) :509-512
[7]   Phenylboronic acid as a mild and efficient catalyst for Biginelli reaction [J].
Debache, Abdelmadjid ;
Boumoud, Boudjemaa ;
Amimour, Mouna ;
Belfaitah, Ali ;
Rhouati, Salah ;
Carboni, Bertrand .
TETRAHEDRON LETTERS, 2006, 47 (32) :5697-5699
[8]   Recent developments in isocyanide based multicomponent reactions in applied chemistry [J].
Dömling, A .
CHEMICAL REVIEWS, 2006, 106 (01) :17-89
[9]   New three-component reaction:: Novel formation of a seven-membered ring by the unexpected reaction at the γ-position of the β-keto ester [J].
Fujioka, Hiromichi ;
Murai, Kenichi ;
Kubo, Ozora ;
Ohba, Yusuke ;
Kita, Yasuyuki .
ORGANIC LETTERS, 2007, 9 (09) :1687-1690
[10]   Enantioselective organocatalytic intramolecular aza-Michael reaction:: a concise synthesis of (+)-sedamine., (+)-allosedamine, and (+)-coniine [J].
Fustero, Santos ;
Jimenez, Diego ;
Moscardo, Javier ;
Catalan, Silvia ;
del Pozo, Carlos .
ORGANIC LETTERS, 2007, 9 (25) :5283-5286