A facile and efficient synthesis of 3,5-disubstituted tetronic acids in aqueous media involving acid-catalyzed intramolecular oxa-pyridylethylation

被引：24

作者：

Bi, XH ^{[1
]}

Liu, Q ^{[1
]}

Sun, SG ^{[1
]}

Liu, J ^{[1
]}

Pan, W ^{[1
]}

Zhao, L ^{[1
]}

Dong, DW ^{[1
]}

机构：

[1] NE Normal Univ, Dept Chem, Changchun 130024, Peoples R China

来源：

SYNLETT | 2005年 / 01期

关键词：

aqueous media; tetronic acid derivatives; alpha-oxo ketene-S; S-acetals; oxa-pyridylethylation; alpha-oxo ketene-N; N-acetals;

D O I：

10.1055/s-2004-836034

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile and efficient one-pot synthesis of 3-[bis(alkylthio/alkylamino)methylene]-5-(pyridyl/quinoylmethyl) furan-2,4(3H,5H)-diones 3 and 10, based on a sequential aldol condensation and lactonization reaction between alpha-oxo ketene-S,S-acetals 1 and pyridine/qinoline-carboxaldehydes 2 in aqueous media, has been developed. A mechanism involving an acid-catalyzed intramolecular oxa-pyridylethylation reaction is proposed for the formation of the lactone ring.

引用

页码：49 / 54

页数：6

共 59 条

[31] Langer P, 2000, SYNLETT, P844
[32] Efficient synthesis of γ-alkylidenetetronic esters by sequential Lewis acid catalyzed [3+2] cyclizations and palladium-catalyzed cross-coupling reactions
Langer, P
Eckardt, T
Schneider, T
Göbel, C
Herbst-Irmer, R
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (07) : 2222 - 2226
[33] THE DIRECT PYRIDYLETHYLATION OF ACTIVE HYDROGEN COMPOUNDS .1. 2-VINYLPYRIDINE WITH KETONES
LEVINE, R
WILT, MH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (02) : 342 - 344
[34] Cytotoxic pyrrolo- and furanoterpenoids from the sponge Sarcotragus species
Liu, YH
Hong, JK
Lee, CO
Im, KS
Kim, ND
Choi, JS
Jung, JH
[J]. JOURNAL OF NATURAL PRODUCTS, 2002, 65 (09): : 1307 - 1314
[35] Routes to building blocks for heterocyclic synthesis by reduction of ketene dithioacetals
Mellor, JM
Schofield, SR
Korn, SR
[J]. TETRAHEDRON, 1997, 53 (50) : 17151 - 17162
[36] Regioselective ring opening of malic acid anhydrides by carbon nucleophiles. Application in the synthesis of chiral tetronic acids
Mitsos, CA
Zografos, AL
Igglessi-Markopoulou, O
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (18) : 5852 - 5853
[37] EPR studies of nitrogen-centred free radicals. Part 50. Unusual decomposition behaviour of isolable stable thioaminyl free radicals at high temperature
Miura, Y
Momoki, M
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1998, (05): : 1185 - 1188
[38] NANDI S, 2002, J ORG CHEM, V67, P14
[39] ADDITION OF TRICHLOROSILANE TO STYRENE, 2-VINYLPYRIDINE, ALLYLCYANIDE AND OCTENE-1 .7.
NOZAKURA, S
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1956, 29 (07) : 784 - 789
[40] Paintner FF, 2003, SYNLETT, P83

← 1 2 3 4 5 6 →