Synthesis of tetrasubstituted pyridines by the acid-catalysed Bohlmann-Rahtz reaction

被引：73

作者：

Bagley, MC

Brace, C

Dale, JW

Ohnesorge, M

Phillips, NG

Xiong, X

Bower, J

机构：

[1] Cardiff Univ, Dept Chem, Cardiff CF10 3TB, S Glam, Wales

[2] RiboTargets Ltd, Cambridge CB1 6GB, England

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2002年 / 14期

关键词：

D O I：

10.1039/b203397f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New facile experimental procedures for the preparation of 2,3,4,6-tetrasubstituted pyridines in a single synthetic step have been developed. Thus, an enamino ester and alkynone react by Michael addition-cyclodehydration in a heterocyclisation process that is catalysed by acetic acid, Amberlyst 15 ion exchange resin, zinc(II) bromide or ytterbium(III) triflate. The new one-step Bronsted or Lewis acid-catalysed Bohlmann-Rahtz reaction is a simple, direct and highly expedient method for the synthesis of pyridines that proceeds at a lower reaction temperature and avoids the need to isolate reaction intermediates.

引用

页码：1663 / 1671

页数：9

共 21 条

[1] The synthesis of novel heterocyclic substituted α-amino acids;: further exploitation of α-amino acid alkynyl ketones as reactive substrates
Adlington, RM
Baldwin, JE
Catterick, D
Pritchard, GJ
Tang, LT
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (15): : 2311 - 2316
[2] Bagley MC, 2001, SYNLETT, P1523
[3] A new and highly expedient synthesis of pyrido[2,3-d]pyrimidines
Bagley, MC
Hughes, DD
Lloyd, R
Powers, VEC
[J]. TETRAHEDRON LETTERS, 2001, 42 (37) : 6585 - 6588
[4] Bagley MC, 2001, SYNLETT, P1149
[5] Total synthesis of the thiopeptide promothiocin A
Bagley, MC
Bashford, KE
Hesketh, CL
Moody, CJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (14) : 3301 - 3313
[6] BARALDI PG, 1983, SYNTHESIS-STUTTGART, P902
[7] UBER EINE NEUE PYRIDINSYNTHESE
BOHLMANN, F
RAHTZ, D
[J]. CHEMISCHE BERICHTE-RECUEIL, 1957, 90 (10): : 2265 - 2272
[8] BRAM G, 1964, B SOC CHIM FR, P945
[9] NOVEL SYNTHESIS OF 2-OXO-4-PHENYL-3-BUTYNOIC ACID, A NEW INHIBITOR AND ALTERNATE SUBSTRATE OF PYRUVATE DECARBOXYLASE
CHIU, CFC
JORDAN, F
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (19) : 5763 - 5766
[10] The reaction of 2-(tetrazol-5-yl)alkyl ketones and of 2-(tetrazol-5-yl)alkanoic acid derivatives with lead tetraacetate.: A novel method of preparation of alk-2-ynyl ketones and alk-2-ynoic acid derivatives
Fetter, J
Nagy, I
Giang, LT
Kajtár-Peredy, M
Rockenbauer, A
Korecz, L
Czira, G
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, Royal Society of Chemistry (09): : 1131 - 1139

← 1 2 3 →