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

[21] Synthesis of Novel 2-(N-Substituted)imino-2,5-dihydrofuran-3-carboxamides Containing a Thiourea Residue and an Oxothiazolidinylidene Ring
Karapetyan, L., V
Tokmajyan, G. G.
Makaryan, G. M.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 55 (11) : 1806 - 1808
[22] A new synthesis and application of N,N′-dibromo-N,N′-1,2-ethylene bis(2,5-dimethyl benzene sulfonamide);: As a novel selective bromination agent for aromatic compounds.
Ardeshir, K
Abbas, S
SYNTHETIC COMMUNICATIONS, 1999, 29 (23) : 4079 - 4085
[23] Novel Synthesis of Substituted 2-Trifluoromethyl and 2-Perfluoroalkyl N-Arylpyridinium Compounds-Mechanistic Insights
El Kharrat, Salem
Laurent, Philippe
Boiteau, Laurent
Blancou, Hubert
MOLECULES, 2019, 24 (12):
[24] A novel synthesis of functionalized sulfonamide derivatives using the reaction of substituted thiourea or oxime derivatives with N-(2,3-dibromopropyl)-aryl(alkyl)sulfonamides
Monfared, Ali
Khalili, Gholamhossein
MONATSHEFTE FUR CHEMIE, 2023, 154 (01): : 123 - 130
[25] A novel synthesis of functionalized sulfonamide derivatives using the reaction of substituted thiourea or oxime derivatives with N-(2,3-dibromopropyl)-aryl(alkyl)sulfonamides
Ali Monfared
Gholamhossein Khalili
Monatshefte für Chemie - Chemical Monthly, 2023, 154 : 123 - 130
[26] ANTITUMOR AGENTS .141. SYNTHESIS AND BIOLOGICAL EVALUATION OF NOVEL THIOCOLCHICINE ANALOGS - N-ACYL-(SUBSTITUTED BENZYL)DEACETYLTHIOCOLCHICINES, AND N-AROYL-(SUBSTITUTED BENZYL)DEACETYLTHIOCOLCHICINES, AND (SUBSTITUTED BENZYL)DEACETYLTHIOCOLCHICINES AS POTENT CYTOTOXIC AND ANTIMITOTIC COMPOUNDS
SUN, L
HAMEL, E
LIN, CM
HASTIE, SB
PYLUCK, A
LEE, KH
JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (10) : 1474 - 1479
[27] Synthesis, biological evaluation and in silico studies of novel N-substituted phthalazine sulfonamide compounds as potent carbonic anhydrase and acetylcholinesterase inhibitors
Turkes, Cuneyt
Arslan, Mustafa
Demir, Yeliz
Cocaj, Liridon
Nixha, Arleta Rifati
Beydemir, Sukru
BIOORGANIC CHEMISTRY, 2019, 89
[28] DESIGN, SYNTHESIS, AND CYTOTOXIC ACTIVITY OF SOME NOVEL N-(SUBSTITUTED) BENZAMIDE DERIVATIVES BEARING COUMARIN AND 1-AZOCOUMARIN COMPOUNDS
Al-Hazmi, Ghaferah H.
BULLETIN OF THE CHEMICAL SOCIETY OF ETHIOPIA, 2023, 37 (04) : 1003 - 1019
[29] Novel catenated N6 energetic compounds based on substituted 1,2,4-triazoles: synthesis, structures and properties
Li, Yanan
Wang, Bin
Chang, Pei
Hu, Jianjian
Chen, Tao
Wang, Yinglei
Wang, Bozhou
RSC ADVANCES, 2018, 8 (25) : 13755 - 13763
[30] Cyclization of Activated Methylene Isocyanides with MethylN(N),N′-Di(tri)substituted Carbamimidothioate: A Novel Entry for the Synthesis of N,1-Aryl-4-tosyl/ethoxycarbonyl-1 H-imidazol-5-amines
Dukanya
Swaroop, Toreshettahally R.
Rangappa, Shobith
Rangappa, Kanchugarakoppal S.
Basappa
SYNOPEN, 2019, 3 (03): : 71 - 76

← 1 2 3 4 5 →