Catalyst- and solvent-free regioselective ring opening of aziridines with amines: application in the gram-scale synthesis of the α,β-diamino propionic derivative, aspergillomarasmine A

被引：2

作者：

Lin, Xing ^{[1
]}

Zhang, Dajun ^{[1
]}

Li, Jing ^{[1
]}

Zhang, Lei ^{[1
]}

机构：

[1] South China Univ Technol, Sch Biol & Biol Engn, Guangzhou 510006, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2023年 / 21卷 / 24期

关键词：

ORTHOGONALLY PROTECTED AZALANTHIONINES; BETA-CYCLODEXTRIN; POTASSIUM THIOCYANATE; N-TOSYLAZIRIDINES; FLUORESCENT-PROBE; EFFICIENT; WATER; INHIBITOR; EPOXIDES; THIOLS;

D O I：

10.1039/d3ob00722g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A green and efficient approach for synthesizing alpha,beta-diamino propionic derivatives was developed through the ring opening of alpha-C-alkyloxycarbonyl aziridine. This method features catalyst- and solvent-free conditions, high regioselectivity, and wide substrate scope including solid amines, and realizes the gram-scale synthesis of aspergillomarasmine A.

引用

页码：4977 / 4981

页数：5

共 35 条

[21] Solvent-Free Synthesis and Key Intermediate Isolation in Ni2Dy2 Catalyst Development in the Domino Ring-Opening Electrocyclization Reaction of Furfural and Amines
Sampani, Stavroula I.
McGown, Andrew
Vargas, Alfredo
Abdul-Sada, Alaa
Tizzard, Graham J.
Coles, Simon J.
Spencer, John
Kostakis, George E.
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (11): : 6858 - 6867
[22] Highly efficient regioselective synthesis of pyrroles via a tandem enamine formation-Michael addition-cyclization sequence under catalyst- and solvent-free conditions
Vivekanand, Thavaraj
Vinoth, Perumal
Agieshkumar, B.
Sampath, Natarajan
Sudalai, Arumugam
Menendez, Carlos
Sridharan, Vellaisamy
GREEN CHEMISTRY, 2015, 17 (06) : 3415 - 3423
[23] Alkylsulfonic acid functionalized aluminoborate: A highly efficient and regioselective solid acid catalyst for ring-opening addition of epoxide under solvent-free condition
Yang, Jing
Sun, Yurong
Yang, Yao
Gao, Wenliang
Yang, Tao
MOLECULAR CATALYSIS, 2024, 569
[24] Mild Organic Ammonium Tribromide-Mediated Regioselective Ring Opening of Epoxides with Alcohols, Water, Acetic Anhydride, and Amines Under Solvent-Free Reaction Conditions
Singhal, Sweety
Jain, Suman L.
Sain, Bir
SYNTHETIC COMMUNICATIONS, 2011, 41 (12) : 1829 - 1837
[25] Regioselective ring-opening reaction of 1,2-epoxides with arylselenol under solvent-free conditions and application to the synthesis of 1,3-oxazolidin-2-ones
Yang, MH
Yuan, CY
Pan, Y
Zhu, CJ
CHINESE JOURNAL OF CHEMISTRY, 2006, 24 (05) : 669 - 673
[26] Solvent-controlled C2/C3-regioselective ring-opening/coupling of aziridines with amines and CS2: synthesis of 2-aminoethyl dithiocarbamates
Li, Wenxue
Yang, Xueying
Miao, Man
Sun, Fengkai
Yuan, Hui
Lan, Xiao-Bing
Yu, Jian-Qiang
Zhang, Jian
An, Zhenyu
ORGANIC CHEMISTRY FRONTIERS, 2025, 12 (04): : 1266 - 1273
[27] Alumina-supported molybdenum (VI) oxide: An efficient and recyclable heterogeneous catalyst for regioselective ring opening of epoxides with thiols, acetic anhydride, and alcohols under solvent-free conditions
Singhal, Sweety
Jain, Suman L.
Sain, Bit
CHEMISTRY LETTERS, 2008, 37 (06) : 620 - 621
[28] A new role for solar energy as a renewable energy source for catalyst-solvent free gram-scale synthesis of pyrano[2,3-d]pyrimidine scaffolds
Mohamadpour, Farzaneh
RESEARCH ON CHEMICAL INTERMEDIATES, 2023, 49 (09) : 3881 - 3891
[29] A new role for solar energy as a renewable energy source for catalyst-solvent free gram-scale synthesis of pyrano[2,3-d]pyrimidine scaffolds
Farzaneh Mohamadpour
Research on Chemical Intermediates, 2023, 49 : 3881 - 3891
[30] Regioselective ring opening of epoxides using NH4SCN/silica sulfuric acid:An efficient approach for the synthesis of β-hydroxy thiocyanate under solvent-free conditions
Ali R. Kiasat
Maryam Zayadi
Mehdi Fallah Mehrjardi
Chinese Chemical Letters, 2008, (06) : 665 - 668

← 1 2 3 4 →