A Concise Synthetic Method for Constructing 3-Substituted Piperazine-2-Acetic Acid Esters from 1,2-Diamines

被引：6

作者：

Chamakuri, Srinivas ^{[1
]}

Tang, Sunny Ann ^{[1
]}

Tran, Kevin A. ^{[1
]}

Guduru, Shiva Krishna Reddy ^{[1
]}

Bolin, Peter K. ^{[1
]}

MacKenzie, Kevin R. ^{[1
,2
]}

Young, Damian W. ^{[1
,2
,3
]}

机构：

[1] Baylor Coll Med, Ctr Drug Discovery, Dept Pathol & Immunol, One Baylor Plaza, Houston, TX 77030 USA

[2] Baylor Coll Med, Dept Pharmacol & Chem Biol, One Baylor Plaza, Houston, TX 77030 USA

[3] Baylor Coll Med, Verna & Marrs McLean Dept Biochem & Mol Biol, Houston, TX 77030 USA

来源：

MOLECULES | 2022年 / 27卷 / 11期

关键词：

chiral piperazines; 2; 3-substituted piperazines; diamine; annulation; masamune condensation; ASYMMETRIC-SYNTHESIS; BUILDING-BLOCKS; INHIBITORS;

D O I：

10.3390/molecules27113419

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

We report a short synthetic route for synthesizing 2,3-substituted piperazine acetic acid esters. Optically pure amino acids were efficiently converted into 1,2-diamines that could be utilized to deliver the title 2,3-substituted piperazines in five steps with a high enantiomeric purity. The novel route facilitated, for the first time, the synthesis of 3-phenyl substituted-2-piperazine acetic acid esters that were difficult to achieve using other methods; however, in this case, the products underwent racemization.

引用

页数：8

共 7 条

[1] Synthesis of Enantiomerically Pure 3-Substituted Piperazine-2-acetic Acid Esters as Intermediates for Library Production
Guduru, Shiva Krishna Reddy
Chamakuri, Srinivas
Raji, Idris O.
MacKenzie, Kevin R.
Santini, Conrad
Young, Damian W.
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (19): : 11777 - 11793
[2] Convenient Synthesis of 1,2-Diamines from β-Chloro Amines: Precursors of New Substituted Piperazin-2-ones
Slama, Soumaya
Elemine, Brahim Ould
Besbes, Rafaa
SYNTHETIC COMMUNICATIONS, 2013, 43 (17) : 2286 - 2293
[3] Ga(ClO4)3-catalyzed Reaction of 1,2-Diamines and α-Bromoketones: Synthesis of 2-Substituted Quinoxalines
Ji Yun-fei
Chen Tang-ming
Mao Hai-feng
Zou Jian-ping
CHEMICAL RESEARCH IN CHINESE UNIVERSITIES, 2012, 28 (04) : 642 - 646
[4] AN EFFICIENT ONE-POT SYNTHESIS OF (1,2-DIHYDRO-2-OXOQUINOXALINE-3-YL) METHYL CARBAMODITHIOATE DERIVATIVES FROM BENZENE-1,2-DIAMINES, ETHYL BROMOPYRUVATE, CS2, AND SECONDARY AMINES
Piltan, Mohammad
Zarei, Seyed Amir
Saydi, Hassan
Kalantari, Shahin
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2015, 190 (11) : 1814 - 1819
[5] Synthesis of Substituted Imidazo[1,2-a]Pyridin-3-yl-Acetic Acids by Multicomponent Condensation of 2-Aminopyridines with Arylglyoxals and Meldrum's Acid
Lichitsky, Boris V.
Tretyakov, Aleksander D.
Komogortsev, Andrey N.
Mityanov, Vitaly S.
Dudinov, Arkady A.
Krayushkin, Mikhail M.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2019, 55 (02) : 156 - 159
[6] Stereochemical aspects and the synthetic scope of the SHi at the sulfur atom. Preparation of enantiopure 3-substituted 2,3-dihydro-1,2-benzoisothiazole 1-oxides and 1,1-dioxides
Fernandez-Salas, Jose A.
Mercedes Rodriguez-Fernandez, M.
Carmen Maestro, M.
Garcia-Ruano, Jose L.
CHEMICAL COMMUNICATIONS, 2014, 50 (45) : 6046 - 6048
[7] Supported Palladium Nanoparticles-Catalyzed Synthesis of 3-Substituted 2-Quinolones from 2-Iodoanilines and Alkynes Using Oxalic Acid as C1 Source
Thakur, Vandna
Sharma, Ajay
Yamini
Sharma, Nishtha
Das, Pralay
ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (03) : 426 - 431

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