Isothiouronium-Mediated Conversion of Carboxylic Acids to Cyanomethyl Thioesters

被引：6

作者：

Maulide, Nuno ^{[1
]}

Tiefenbrunner, Irmgard ^{[1
]}

Brutiu, Bogdan R. ^{[1
]}

Stopka, Tobias ^{[1
]}

机构：

[1] Univ Vienna, Inst Organ Chem, A-1090 Vienna, Austria

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 06期

基金：

奥地利科学基金会; 欧洲研究理事会;

关键词：

THIOACETIC ACID; UBIQUITIN; ALDEHYDES; THIOLS;

D O I：

10.1021/acs.joc.2c02902

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report the development of an isothiouronium salt as a reagent for the operationally simple synthesis of cyanomethyl thioesters with high functional group tolerance and avoiding the use of thiols. Additionally, we show that the products can be engaged in amide synthesis in either a two-step or one-pot fashion.

引用

页码：3941 / 3944

页数：4

共 38 条

[1] Palladium-Catalyzed Thiocarbonylation of Alkenes toward Linear Thioesters [J].

Ai, Han-Jun ;

Zhao, Fengqian ;

Geng, Hui-Qing ;

Wu, Xiao-Feng .

ACS CATALYSIS, 2021, 11 (06) :3614-3619

[2] Citric Acid Cycle and Role of its Intermediates in Metabolism [J].

Akram, Muhammad .

CELL BIOCHEMISTRY AND BIOPHYSICS, 2014, 68 (03) :475-478

[3] 2-mercaptopyridine-1-oxide-based peptide coupling reagents [J].

Albericio, F ;

Bailén, MA ;

Chinchilla, R ;

Dodsworth, DJ ;

Nájera, C .

TETRAHEDRON, 2001, 57 (47) :9607-9613

[4] 2-mercaptopyridone 1-oxide-based uronium salts:: New peptide coupling reagents [J].

Bailén, MA ;

Chinchilla, R ;

Dodsworth, DJ ;

Nájera, C .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (24) :8936-8939

[5] Efficient synthesis of primary amides using 2-mercaptopyridone-1-oxide-based uronium salts [J].

Bailén, MA ;

Chinchilla, R ;

Dodsworth, DJ ;

Nájera, C .

TETRAHEDRON LETTERS, 2000, 41 (50) :9809-9813

[6] Dess-Martin periodinane mediated synthesis of thioesters from aldehydes [J].

Bandgar, Sunita B. ;

Bandgar, B. P. ;

Korbad, B. L. ;

Sawant, S. S. .

TETRAHEDRON LETTERS, 2007, 48 (07) :1287-1290

[7] Nonproteolytic Functions of Ubiquitin in Cell Signaling [J].

Chen, Zhijian J. ;

Sun, Lijun J. .

MOLECULAR CELL, 2009, 33 (03) :275-286

[8] Poly(3,4-dimethyl-5-vinylthiazolium)/DBU-Catalyzed Thioesterification of Aldehydes with Thiols [J].

Chung, Junyong ;

Seo, Ue Ryung ;

Chun, Supill ;

Chung, Young Keun .

CHEMCATCHEM, 2016, 8 (02) :318-321

[9]

Collier S. J., 2007, CATEGORY 3 COMPOUNDS, V20, P1597, DOI DOI 10.1055/S0S-SD-020-01480

[10] TOXIN-TARGETED DESIGN FOR ANTICANCER THERAPY .1. SYNTHESIS AND BIOLOGICAL EVALUATION OF NEW THIOIMIDATE HETEROBIFUNCTIONAL REAGENTS [J].

DELPRINO, L ;

GIACOMOTTI, M ;

DOSIO, F ;

BRUSA, P ;

CERUTI, M ;

GROSA, G ;

CATTEL, L .

JOURNAL OF PHARMACEUTICAL SCIENCES, 1993, 82 (05) :506-512

← 1 2 3 4 →