A Three-Component Ugi-Type Reaction of N-Carbamoyl Imines Enables a Broad Scope Primary α-Amino 1,3,4-Oxadiazole Synthesis

被引：10

作者：

Matheau-Raven, Daniel ^{[1
]}

Boulter, Elizabeth ^{[1
]}

Rogova, Tatiana ^{[1
]}

Dixon, Darren J. ^{[1
]}

机构：

[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 21期

基金：

英国工程与自然科学研究理事会; 加拿大自然科学与工程研究理事会;

关键词：

IMIDAZOLE-1-SULFONYL AZIDE; DERIVATIVES; NITROGEN; QUANTIFICATION; HETEROCYCLES; DIVERSITY; ALDEHYDES; EFFICIENT; SCALES;

D O I：

10.1021/acs.orglett.1c02945

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general synthesis of N-protected primary alpha-amino 1,3,4-oxadiazoles, from N-carbamoyl imines, N-isocyanimino-triphenylphosphorane (NIITP), and carboxylic acids, is described. Featuring an isocyanide addition reaction with N-carbamoyl imines, this efficient three-component Ugi-type reaction was found to be broad in scope with respect to imine, and carboxylic acid coupling partners. Furthermore, the versatility of this method was demonstrated by alpha-amino 1,2,4-triazole synthesis, the late-stage functionalization of seven drug molecules, and five divergent derivatizations of a primary alpha-amino 1,3,4-oxadiazole.

引用

页码：8209 / 8213

页数：5

共 50 条

[1] Study on the propylphosphonic anhydride (T3P®) mediated Ugi-type three-component reaction. Efficient synthesis of an α-amino amide library
Milen, Matyas
Dancso, Andras
Foldesi, Tamas
Volk, Balazs
TETRAHEDRON, 2017, 73 (01) : 70 - 77
[2] Three-Component 1,4-Addition through Ugi-Type Reaction, an Oxidative Dearomatization Strategy
Chen, Zhihao
Liu, Yuqing
Gao, Xing
Sun, Yuanyuan
Lei, Lingyu
Zhao, Xia
Lu, Kui
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 13 (01)
[3] A p-toluenesulfinic acid-catalyzed three-component Ugi-type reaction and its application for the synthesis of α-amino amides and amidines
Saha, Biswajit
Frett, Brendan
Wang, Yuanxiang
Li, Hong-yu
TETRAHEDRON LETTERS, 2013, 54 (19) : 2340 - 2343
[4] One-pot three-component reaction for the synthesis of novel series of fully substituted 1,3,4-oxadiazole derivatives bearing pyridine moiety
Souldozi, Ali
Karami, Samad
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2016, 191 (06) : 867 - 870
[5] A novel four-component reaction for the synthesis of disubstituted 1,3,4-oxadiazole derivatives
Ali Ramazani
Nahid Shajari
Amir Mahyari
Yavar Ahmadi
Molecular Diversity, 2011, 15 : 521 - 527
[6] A novel four-component reaction for the synthesis of disubstituted 1,3,4-oxadiazole derivatives
Ramazani, Ali
Shajari, Nahid
Mahyari, Amir
Ahmadi, Yavar
MOLECULAR DIVERSITY, 2011, 15 (02) : 521 - 527
[7] The Reaction of (N-isocyanimino) triphenylphosphorane with an Electron-poor α-Haloketone in the Presence of Aromatic Carboxylic Acids: A Novel Three-Component Reaction for the Synthesis of Disubstituted 1,3,4-oxadiazole Derivatives
Ramazani, Ali
Ahmadi, Yavar
Rouhani, Morteza
Shajari, Nahid
Souldozi, Ali
HETEROATOM CHEMISTRY, 2010, 21 (06) : 368 - 372
[8] Facile microwave-assisted synthesis of benzimidazole scaffolds via Ugi-type three-component condensation (3CC) reactions
Gui-Ting Song
Zhi-Gang Xu
Dian-Yong Tang
Shi-Qiang Li
Zhi-Gang Xie
Hong-Liang Zhong
Zhi-Wei Yang
Jin Zhu
Jin Zhang
Zhong-Zhu Chen
Molecular Diversity, 2016, 20 : 575 - 580
[9] Facile microwave-assisted synthesis of benzimidazole scaffolds via Ugi-type three-component condensation (3CC) reactions
Song, Gui-Ting
Xu, Zhi-Gang
Tang, Dian-Yong
Li, Shi-Qiang
Xie, Zhi-Gang
Zhong, Hong-Liang
Yang, Zhi-Wei
Zhu, Jin
Zhang, Jin
Chen, Zhong-Zhu
MOLECULAR DIVERSITY, 2016, 20 (02) : 575 - 580
[10] One-pot, Three-component Synthesis of Fully Substituted 1,3,4-Oxadiazole Derivatives from (N-Isocyanoimino)triphenylphosphorane, Aromatic Carboxylic acids and (1R)-(-)-Campherchinon
Ramazani, Ali
Nasrabadi, Fatemeh Zeinali
Abdian, Behnaz
Rouhani, Morteza
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2012, 33 (02) : 453 - 458

← 1 2 3 4 5 →