Novel one-step synthesis of 2-carbonyl/thiocarbonyl isoindolinones and mechanistic disclosure on the rearrangement reaction of o-phthalaldehyde with amide/thioamide analogs

被引：41

作者：

Wan, Jieping ^{[1
]}

Wu, Bin ^{[1
]}

Pan, Yuanjiang ^{[1
]}

机构：

[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China

来源：

TETRAHEDRON | 2007年 / 63卷 / 38期

基金：

中国国家自然科学基金;

关键词：

2-carbonyl isoindolinone; 2-thiocarbonyl isoindolinone; rearrangement; mechanism;

D O I：

10.1016/j.tet.2007.07.009

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A rearrangement reaction of o-phthalaldehyde with urea/thiourea analogs or amides/thioamides under the catalysis of TMSC1 (trimethylchlorosilane) is described, whereby a series of 2-carbonyl isoindolinones and 2-thiocarbonyl isoindolinones are afforded. This is the first time that the N-carbonyl/thiocarbonyl isoindolinones are synthesized in a single step from o-phthalaldehyde. Similar reactions using primary amines also proceed smoothly to give corresponding N-alkyl or N-aryl isoindolinones in this mild catalytic system. The mechanism of this kind of rearrangement is discussed based on new evidences observed from the ESI-MS time-interval monitoring of the full reaction course and deuterium exchange experiments. (C) 2007 Elsevier Ltd. All rights reserved.

引用

页码：9338 / 9344

页数：7

共 54 条

[41] Lipase-catalyzed dynamic kinetic resolution of hemiaminals [J].

Sharfuddin, M ;

Narumi, A ;

Iwai, Y ;

Miyazawa, K ;

Yamada, S ;

Kakuchi, T ;

Kaga, H .

TETRAHEDRON-ASYMMETRY, 2003, 14 (11) :1581-1585

[42] ELECTROORGANIC CHEMISTRY .83. A NOVEL ELECTROGENERATED BASE - ALKYLATION OF METHYL ARYLACETATES AT THE ALPHA-METHYLENE GROUP [J].

SHONO, T ;

KASHIMURA, S ;

NOGUSA, H .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (11) :2043-2045

[43] REACTION OF ORTHO-PHTHALALDEHYDE AND THIOLS WITH PRIMARY AMINES - FORMATION OF 1-ALKYL(AND ARYL)THIO-2-ALKYLISOINDOLES [J].

SIMONS, SS ;

JOHNSON, DF .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (14) :2886-2891

[44] CONVENIENT PREPARATION OF 11H-BENZO[A]FLUORENONE AND 11H-BENZO[B]FLUORENONE [J].

STREITWIESER, A ;

BROWN, SM .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (04) :904-906

[45] Reaction systems peripheral to the 1:2 Mannich condensation reaction between o-phthalaldehyde and primary amine [J].

Takahashi, I ;

Nishiuchi, K ;

Miyamoto, R ;

Hatanaka, M ;

Uchida, H ;

Isa, K ;

Sakushima, A ;

Hosoi, S .

LETTERS IN ORGANIC CHEMISTRY, 2005, 2 (01) :40-43

[46]

Takahashi I, 1996, SYNLETT, P353

[47] PHTHALIMIDYLBENZENESULFONYL CHLORIDES AS FLUORESCENCE LABELING REAGENTS FOR AMINO-ACIDS IN HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY [J].

TSURUTA, Y ;

DATE, Y ;

KOHASHI, K .

JOURNAL OF CHROMATOGRAPHY, 1990, 502 (01) :178-183

[48] Synthesis and structure-activity relationships of novel pyrrolocarbazole lactam analogs as potent and cell-permeable inhibitors of poly(ADP-ribose)polymerase-1 (PARP-1) [J].

Wells, GJ ;

Bihovsky, R ;

Hudkins, RL ;

Ator, MA ;

Husten, J .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (05) :1151-1155

[49] Dynamic kinetic resolution of hemiaminals with axially chiral twisted amides [J].

Yamada, S ;

Noguchi, E .

TETRAHEDRON LETTERS, 2001, 42 (21) :3621-3624

[50] Highly chemoselective multicomponent Biginelli-type condensations of cycloalkanones, urea or thiourea and aldehydes [J].

Zhu, YL ;

Huang, SL ;

Pan, YJ .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (11) :2354-2367

← 1 2 3 4 5 6 →