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 [J].

Langer, P ;

Eckardt, T ;

Schneider, T ;

Göbel, C ;

Herbst-Irmer, R .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (07) :2222-2226

[33] THE DIRECT PYRIDYLETHYLATION OF ACTIVE HYDROGEN COMPOUNDS .1. 2-VINYLPYRIDINE WITH KETONES [J].

LEVINE, R ;

WILT, MH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (02) :342-344

[34] Cytotoxic pyrrolo- and furanoterpenoids from the sponge Sarcotragus species [J].

Liu, YH ;

Hong, JK ;

Lee, CO ;

Im, KS ;

Kim, ND ;

Choi, JS ;

Jung, JH .

JOURNAL OF NATURAL PRODUCTS, 2002, 65 (09) :1307-1314

[35] Routes to building blocks for heterocyclic synthesis by reduction of ketene dithioacetals [J].

Mellor, JM ;

Schofield, SR ;

Korn, SR .

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 [J].

Mitsos, CA ;

Zografos, AL ;

Igglessi-Markopoulou, O .

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 [J].

Miura, Y ;

Momoki, M .

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. [J].

NOZAKURA, S .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1956, 29 (07) :784-789

[40]

Paintner FF, 2003, SYNLETT, P83

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