N,N′-Di-Boc-Substituted Thiourea as a Novel and Mild Thioacylating Agent Applicable for the Synthesis of Thiocarbonyl Compounds

被引：6

作者：

Yin, Biao-Lin ^{[1
]}

Liu, Zhao-Gui ^{[2
]}

Zhang, Jian-Cun ^{[2
]}

Li, Zheng-Rong ^{[1
]}

机构：

[1] S China Univ Technol, Sch Chem & Chem Engn, Guangzhou 510640, Peoples R China

[2] Chinese Acad Sci, Guangzhou Inst Biomed & Hlth, Guangzhou 510663, Guangdong, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2010年 / 06期

基金：

国家教育部博士点专项基金资助;

关键词：

N; N '-di-Boc-substituted thiourea; thioacylating agent; thiocarbonyl; TERTIARY AMIDES; SECONDARY; CONVERSION; DERIVATIVES;

D O I：

10.1055/s-0029-1219273

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stable and readily available N,N'-di-Boc-substituted thiourea, when activated with trifluoroacetic acid anhydride, was used as a novel thioacylating agent. Through the thioacylation of nucleophiles, such as amines, alcohols, thiols, sodium benzenethiolate, and sodium malonates with N,N'-di-Boc-substituted thiourea, a series of thiocarbonyl compounds were prepared under mild conditions with good chemical selectivity and functional group tolerance.

引用

页码：991 / 999

页数：9

共 49 条

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OMAR, AMME
ABOULWAFA, OM
LECLERCQ, G
JOURNAL OF PHARMACEUTICAL SCIENCES, 1984, 73 (12) : 1871 - 1873
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Imanishi, T
Obika, S
Nishiyama, T
Nishimoto, M
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BELTRAMI, H
KEAY, JG
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SAMMES, MP
LEUNG, CWF
LEE, CM
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[48] Synthesis and characterization of Mo6 chalcobromides and cyano-substituted compounds built from a novel [(Mo6Bri6Yi2)La6]n- discrete cluster unit (Yi = S or Se and La = Br or CN)
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Salloum, D
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[49] Novel and efficient synthesis of 4,7-dihydro-1H-pyrrolo[2,3-b] pyridine derivatives via one-pot, three-component approach from N-substituted 5-amino-3-cyanopyrroles, various carbonyl and active methylene compounds
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