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

[1] Unusual ring transformation of 2-halogeno-N-phenacylpyridinium salts in reaction with secondary amines:: a facile 'one-pot' route to 1-amino-4-(oxazol-2-yl)butadienes
Babaev, EV
Tsisevich, AA
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (04): : 399 - 401
[2] [4 + 2] cycloaromatization of 4-bis(methylthio)-3-buten-2-one with active methylene ketones: A simple and facile phenol annulation
Barun, O
Nandi, S
Panda, K
Ila, H
Junjappa, H
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (15) : 5398 - 5401
[3] THE PHYSICAL AND CHEMICAL PROPERTIES OF THE METHYLHYDROXYLAMINES
BISSOT, TC
PARRY, RW
CAMPBELL, DH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (04) : 796 - 800
[4] Bühler H, 2000, CHEM-EUR J, V6, P2564, DOI 10.1002/1521-3765(20000717)6:14<2564::AID-CHEM2564>3.0.CO
[5] 2-F
[6] CHOI EB, 1988, SYNTHESIS-STUTTGART, P792
[7] CHOI EB, 1991, SYNTHESIS-STUTTGART, P15
[8] 7-AMINO-5,6,7,8-TETRAHYDROQUINOLINES - PREPARATION FROM 5,6-DIHYDROQUINOLINE AND NITROGEN NUCLEOPHILES
CLIFFE, IA
IFILL, AD
MANSELL, HL
TODD, RS
WHITE, AC
[J]. TETRAHEDRON LETTERS, 1991, 32 (46) : 6789 - 6792
[9] ALPHA-OXO KETENE DITHIOACETALS AND RELATED-COMPOUNDS - VERSATILE 3-CARBON SYNTHONS
DIETER, RK
[J]. TETRAHEDRON, 1986, 42 (12) : 3029 - 3096
[10] ELECTROPHILIC REACTIONS OF 2-VINYLPYRIDINES AND 4-VINYLPYRIDINES
DOERING, WE
WEIL, RAN
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1947, 69 (10) : 2461 - 2466

← 1 2 3 4 5 6 →