N-(SILYLMETHYL)-SUBSTITUTED KETENE N,S-ACETALS AS A SYNTHETIC EQUIVALENT OF NOVEL 1,3-DIPOLAR REAGENT, ALKYLIDENEAZOMETHINE YLIDES - SYNTHESIS AND [3+2]-CYCLOADDITIONS

被引：35

作者：

HOSOMI, A ^{[1
]}

MIYASHIRO, Y ^{[1
]}

YOSHIDA, R ^{[1
]}

TOMINAGA, Y ^{[1
]}

YANAGI, T ^{[1
]}

HOJO, M ^{[1
]}

机构：

[1] NAGASAKI UNIV,FAC PHARMACEUT SCI,NAGASAKI 852,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 19期

关键词：

D O I：

10.1021/jo00306a004

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

: A variety of N-(silylmethyl)-substituted ketene N,S-acetals, readily prepared by the reaction of ketene dithioacetals with ((trimethylsilyl)methyl)amine, followed by N-alkylation, react smoothly with activated alkenes, carbonyl compounds, and thioketones, to afford α-alkylidenepyrrolidines, oxazolidines, and thiazolidines, via a 1,3-elimination of (methylthio)trimethylsilane. These reagents are synthetic equivalents of alkylideneazomethine ylids. © 1990, American Chemical Society. All rights reserved.

引用

页码：5308 / 5310

页数：3

共 50 条

[1] S-SILYLMETHYL-SUBSTITUTED KETENE DITHIOACETALS AS SYNTHETIC EQUIVALENT OF A NOVEL 1,3-DIPOLAR REAGENT, ALKYLIDENETHIOCARBONYL YLIDE - SYNTHESIS AND [3+2] CYCLOADDITION REACTIONS
TOMINAGA, Y
TAKADA, S
KOHRA, S
TETRAHEDRON LETTERS, 1994, 35 (21) : 3555 - 3558
[2] STUDIES ON ORGANOSILICON CHEMISTRY .111. SYNTHESIS AND [3+2]CYCLOADDITIONS OF N-(TRIMETHYLSILYLMETHYL)ISOTHIOUREAS - A SYNTHETIC EQUIVALENT OF NOVEL 1,3-DIPOLAR REAGENT, IMINOAZOMETHINE YLIDE
TOMINAGA, Y
OGATA, K
KOHRA, S
HOJO, M
HOSOMI, A
TETRAHEDRON LETTERS, 1991, 32 (42) : 5987 - 5990
[3] Novel generation of pyridinium ylides from N-(silylmethyl)pyridone analogs via 1,4-silatropy and their 1,3-dipolar cycloadditions leading to N-heteropolycycles
Komatsu, M
Kasano, Y
Yamaoka, S
Minakata, S
SYNTHESIS-STUTTGART, 2003, (09): : 1398 - 1402
[4] Novel synthesis of heterocyclic ketene N,N-, N,O-, and N,S-acetals using cyanoketene dithioacetals
Elgemeie, GH
Elghandour, AH
Abd Elaziz, GW
SYNTHETIC COMMUNICATIONS, 2003, 33 (10) : 1659 - 1664
[5] SYNTHESIS AND [3+2]-CYCLOADDITION REACTION OF 3-[(TRIMETHYLSILYLMETHYLAMINO)(METHYLTHIO)]METHYLENE-2-COUMARANONE AND 3-[(TRIMETHYLSILYLMETHYLAMINO)(METHYLTHIO)]METHYLENE-1-METHYLOXINDOLE - SYNTHETIC EQUIVALENT OF HETEROCYCLIC ALKYLIDENEAZOMETHINE YLIDE AS A NOVEL 1,3-DIPOLAR REAGENT
TOMINAGA, Y
TAKADA, S
KOHRA, S
HETEROCYCLES, 1994, 39 (01) : 15 - 18
[6] ASYMMETRIC-SYNTHESIS OF HIGHLY SUBSTITUTED PYRROLIDINES BY 1,3-DIPOLAR CYCLOADDITIONS OF AZOMETHINE YLIDES WITH N-ACRYLOYLPROLINE BENZYL ESTER
WALDMANN, H
BLASER, E
JANSEN, M
LETSCHERT, HP
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (06): : 683 - 685
[7] Diastereoselective Synthesis of Spiropyrazolones via 1,3-Dipolar [3+2] Cycloadditions between Pyrazolone-Based Olefins and N,N′-Cyclic Azomethine Imines
Tang, Zhe
Wu, Hui-Hui
Xiao-Zu Fan
Zhang, Heng
Cai, Lu-Yu
Bi, Xiao-Fan
Zhao, Hong-Wu
SYNLETT, 2021, 32 (12) : 1201 - 1206
[8] Synthesis of spirotriazolines and spirooxadiazolines via light-induced 1,3-dipolar [3+2] cycloadditions
Jia, Pengfei
Lin, Zhiqian
Luo, Cankun
Liang, Jiao
Lai, Ruizhi
Guo, Li
Yao, Yuan
Wu, Yong
NEW JOURNAL OF CHEMISTRY, 2023, 47 (44) : 20248 - 20252
[9] REACTIONS OF N-(2,2-DIPHENYLVINYLIDEN)METHYLAMINE AND N-(2-METHYL-1-PROPENYLIDENE)ANILINE WITH DICHLOROCARBENE - 1,3-DIPOLAR CYCLO-ADDITION OF KETENE-YLIDES
NOVIKOV, MS
KHLEBNIKOV, AF
KOSTIKOV, RR
ZHURNAL ORGANICHESKOI KHIMII, 1988, 24 (09): : 1917 - 1922
[10] Novel synthesis of N-methyl spiropyrrolidines by 1,3-dipolar cycloaddition reaction of azomethine ylides
Subramaniyan, G
Jayashankaran, J
Raghunathan, R
SYNTHETIC COMMUNICATIONS, 2005, 35 (16) : 2189 - 2193

← 1 2 3 4 5 →