REFORMATSKY REACTION ON ALPHA-OXO KETENE DITHIOACETALS - SYNTHESIS OF SUBSTITUTED AND FUSED ETHYL 2-HYDROXY-6-(METHYLTHIO)BENZOATES, 6-(METHYLTHIO)PYRAN-2-ONES, AND 6-(METHYLTHIO)-2(1H)-PYRIDONE DERIVATIVES

被引：31

作者：

DATTA, A ^{[1
]}

ILA, H ^{[1
]}

JUNJAPPA, H ^{[1
]}

机构：

[1] NE HILL UNIV,DEPT CHEM,SHILLONG 793003,MEGHALAYA,INDIA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 21期

关键词：

D O I：

10.1021/jo00308a015

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel cycloaromatization reaction leading to substituted and annelated ethyl 2-hydroxy-6-(methylthio) benzoates 4 by condensation of a-oxo ketene dithioacetals with an excess of Reformatsky reagent from ethyl bromoacetate through intermediate dienes 3 has been described. The reaction has also been extended for the synthesis of substituted ethyl 3-hydroxy-5-(methyl thio)stilbenecarboxylates 9 by using cinnamoyl ketene dithioacetals 8. A few of the benzoates 4 were desulfurized to the corresponding salicylate derivatives 5. Reaction of acyclic oxo ketene dithioacetals with ethyl(bromozincio)acetate in the presence of cuprous iodide afforded 4- (or 4,5-) substituted 6-(methylthio)pyran-2-ones 15 in moderate to good yields. A probable mechanism for the formation of 15 is suggested. Cyclization of the acyclic dienes 3 or the carbinols 10 with ammonium acetate in refluxing acetic acid afforded the corresponding 4- (or 4,5-) substituted 6-(methylthio)-2(1H)-pyridones 22. © 1990, American Chemical Society. All rights reserved.

引用

页码：5589 / 5594

页数：6

共 19 条

[11] AROMATIC ANNELATION VIA ALPHA-OXOKETENE DITHIOACETALS - SYNTHESIS OF THIORESORCINOL DIMETHYL ETHERS .56.
GUPTA, AK
ILA, H
JUNJAPPA, H
[J]. TETRAHEDRON LETTERS, 1987, 28 (13) : 1459 - 1462
[12] GUPTA AK, 1988, TETRAHEDRON LETT, V29, P6633
[13] ASYMMETRIC SYNTHESES VIA ENANTIOTOPICALLY SELECTIVE HORSE LIVER ALCOHOL-DEHYDROGENASE CATALYZED OXIDATIONS OF DIOLS CONTAINING A PROCHIRAL CENTER
IRWIN, AJ
JONES, JB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (02) : 556 - 561
[14] JUNJAPPA H, IN PRESS TETRAHEDRON
[15] SYNTHESIS OF 2,6-DISUBSTITUTED PYRIDINES, POLYPYRIDINYLS, AND ANNULATED PYRIDINES
POTTS, KT
CIPULLO, MJ
RALLI, P
THEODORIDIS, G
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (16) : 3027 - 3038
[16] CATIONIC BENZOANNELATION OF ACTIVE METHYLENE KETONES VIA OXOKETENDITHIOACETALS
SINGH, G
ILA, H
JUNJAPPA, H
[J]. TETRAHEDRON LETTERS, 1984, 25 (44) : 5095 - 5098
[17] POLARIZED KETENE DITHIOACETALS .42. STUDIES ON THE REACTIONS OF ALKYL AND ARYL GRIGNARD-REAGENTS WITH ALPHA-OXOKETENE DITHIOACETALS
SINGH, G
PURKAYASTHA, ML
ILA, H
JUNJAPPA, H
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (07): : 1289 - 1294
[18] THUILLIER A, 1962, B SOC CHIM FR, P2182
[19] SYNTHESIS AND REACTION OF 6-SUBSTITUTED 3-METHOXYCARBONYL-4-METHYLTHIO-2H-PYRAN-2-ONE DERIVATIVES
TOMINAGA, Y
USHIROGOCHI, A
MATSUDA, Y
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1987, 24 (06) : 1557 - 1567

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