Highly Efficient One-Step Synthesis of N-Trimethylsiloxy Alkyl Imidothioates

被引：8

作者：

Kucinski, Krzysztof ^{[1
]}

Hreczycho, Grzegorz ^{[1
]}

机构：

[1] Adam Mickiewicz Univ, Fac Chem, Ul Umultowska 89b, PL-61614 Poznan, Poland

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 2016卷 / 26期

关键词：

Synthetic methods; Multicomponent reactions; Nitro compounds; Oximes; Sulfur; OXIME ETHERS; SCANDIUM(III) TRIFLATE; BISMUTH(III) TRIFLATE; CYCLIC NITRONES; ARYL HALIDES; NITROALKANES; SILYLATION; ALCOHOLS; THIOLS; HEXAMETHYLDISILAZANE;

D O I：

10.1002/ejoc.201600768

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A hitherto unknown synthetic pathway for the synthesis of N-trimethylsiloxy alkyl imidothioates has been presented. The catalyst-free route uses a range of aromatic, aliphatic, and heterocyclic thiols in the presence of nitroalkanes and hexamethyldisilazane (HMDS). This unusual method expands upon the knowledge of nitro compounds and demonstrates their importance not only as solvents but also as valuable organic reagents. This reaction proceeds under mild conditions and is characterized by excellent yields and a facile workup.

引用

收藏

页码：4577 / 4585

页数：9

相关论文

共 50 条

[41] Chitosan-silica sulfate nanohybrid: a highly efficient and green heterogeneous nanocatalyst for the regioselective synthesis of N-alkyl purine, pyrimidine and related N-heterocycles via presilylated method [J].

Behrouz, Somayeh ;

Rad, Mohammad Navid Soltani ;

Piltan, Mohammad Amin .

CHEMICAL PAPERS, 2020, 74 (01) :113-124

[42] One-step synthesis of biocompatible gold nanoparticles using gallic acid in the presence of poly-(N-vinyl-2-pyrrolidone) [J].

Wang, Wenxing ;

Chen, Qifan ;

Jiang, Cha ;

Yang, Dongzhi ;

Liu, Xingmin ;

Xu, Shukun .

COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS, 2007, 301 (1-3) :73-79

[43] One-pot efficient synthesis of disulfides from alkyl halides and alkyl tosylates using thiourea and elemental sulfur without contamination by higher polysulfides [J].

Abbasi, Mohammad ;

Mohammadizadeh, Mohammad Reza ;

Taghavi, Zeinab Khatoon .

JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2013, 10 (02) :201-205

[44] One-step synthesis of 4-oxoimidazolinium salts from N, N′-diaryl-1,4-diazabuta-1,3-dienes and trialkyl orthoformates [J].

D. V. Pasyukov ;

M. A. Shevchenko ;

V. M. Chernyshev .

Russian Chemical Bulletin, 2023, 72 :1274-1278

[45] Pd/C-catalyzed reductive carbonylation of nitroaromatics for the synthesis of unsymmetrical ureas: one-step synthesis of neburon [J].

Li, Chong-Liang ;

Peng, Jin-Bao ;

Qi, Xinxin ;

Ying, Jun ;

Wu, Xiao-Feng .

NEW JOURNAL OF CHEMISTRY, 2018, 42 (15) :12472-12475

[46] One-step synthesis of 4-oxoimidazolinium salts from N, N′-diaryl-1,4-diazabuta-1,3-dienes and trialkyl orthoformates [J].

Pasyukov, D. V. ;

Shevchenko, M. A. ;

Chernyshev, V. M. .

RUSSIAN CHEMICAL BULLETIN, 2023, 72 (05) :1274-1278

[47] An Efficient Organocatalysis: A One-Pot Highly Enantioselective Synthesis of -Aminophosphonates [J].

Thorat, Prashant B. ;

Goswami, Santosh V. ;

Magar, Rupali L. ;

Patil, Bhagwan R. ;

Bhusare, Sudhakar R. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (24) :5509-5516

[48] One-step Synthesis of Specific pH-responsive Carbon Quantum Dots and Their Luminescence Mechanism [J].

Gao Dong ;

Zhang Yu-Liang ;

Sun Jing ;

Fan Hong-Jun .

JOURNAL OF INORGANIC MATERIALS, 2019, 34 (12) :1309-1315

[49] Star-shaped triarylamines - One-step metal-free synthesis and optoelectronic properties [J].

Meli, Alessandra ;

Ebenhoch, Bernd ;

Kutonova, Ksenia ;

Bihlmeier, Angela ;

Feyrer, Alexander ;

Deck, Eva ;

Breher, Frank ;

Nieger, Martin ;

Colsmann, Alexander ;

Braese, Stefan .

SYNTHETIC METALS, 2019, 256

[50] A novel one-step method for the reductive allylation of esters and the first total synthesis of (±)-erythrococcamide B [J].

Lagoutte, Roman ;

Wilkinson, James A. .

TETRAHEDRON LETTERS, 2010, 51 (52) :6942-6944

← 1 2 3 4 5 →