Microwave-Assisted Stereoselective One-Pot Synthesis of Symmetrical and Unsymmetrical 2,5-Diketopiperazines from Unprotected Amino Acids

被引：40

作者：

Jainta, Manuet ^{[1
]}

Nieger, Martin ^{[2
]}

Braese, Stefan ^{[1
]}

机构：

[1] Univ Karlsruhe, Inst Organ Chem, D-76131 Karlsruhe, Germany

[2] Univ Helsinki, Inorgan Chem Lab, FIN-00014 Helsinki, Finland

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 2008卷 / 32期

关键词：

Amino acids; Diketopiperazines; Heterocycles; Natural products; One-pot reactions; Microwave-assisted organic synthesis (MAOS); Ionic liquids;

D O I：

10.1002/ejoc.200800605

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The facile condensation of unprotected amino acids by a phosphite-promoted one-step coupling reaction is a highly efficient synthesis to generate stereoselective and optically pure symmetrical and unsymmetrical functionalized diketopiperazines. The use of microwaves enhanced by small amounts of ionic liquid is accompanied by significant improvement in reaction times and yields. Simple filtration through a pad of silica provides the pure compounds in very good to excellent yields. ( (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

引用

页码：5418 / 5424

页数：7

共 50 条

[21] A microwave-assisted, propylphosphonic anhydride (T3P®) mediated one-pot Fischer indole synthesis
Desroses, Matthieu
Wieckowski, Krzysztof
Stevens, Marc
Odell, Luke R.
TETRAHEDRON LETTERS, 2011, 52 (34) : 4417 - 4420
[22] One-pot, one-step, catalytic synthesis of 2,5-diformylfuran from fructose
Tao, Furong
Cui, Yuezhi
Yang, Pengfei
Gong, Yinghua
RUSSIAN JOURNAL OF PHYSICAL CHEMISTRY A, 2014, 88 (07) : 1091 - 1096
[23] Efficient microwave-assisted one-pot three-component synthesis of 2,3-disubstituted benzofurans under Sonogashira conditions
Markina, Nataliya A.
Chen, Yu
Larock, Richard C.
TETRAHEDRON, 2013, 69 (13) : 2701 - 2713
[24] One-Pot Conversion of α-Amino Acids into β-Amino Aldehydes or 2-Acetoxyazetidines: Application to the Synthesis of Modified Peptides
Boto, Alicia
Hernandez, Rosendo
Saavedra, Carlos J.
SYNLETT, 2010, (04) : 659 - 663
[25] One-pot, one-step, catalytic synthesis of 2,5-diformylfuran from fructose
Furong Tao
Yuezhi Cui
Pengfei Yang
Yinghua Gong
Russian Journal of Physical Chemistry A, 2014, 88 : 1091 - 1096
[26] One-Pot Synthesis of α-Amino Acids from Imines through CO2 Incorporation: An Alternative Method for Strecker Synthesis
Mita, Tsuyoshi
Chen, Jianyang
Sugawara, Masumi
Sato, Yoshihiro
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (06) : 1393 - 1396
[27] Microwave-assisted one-pot three-component polymerization of alkynes, aldehydes and amines toward amino-functionalized optoelectronic polymers
Jia, Tao
Zheng, Nan-nan
Cai, Wan-qing
Zhang, Jie
Ying, Lei
Huang, Fei
Cao, Yong
CHINESE JOURNAL OF POLYMER SCIENCE, 2017, 35 (02) : 269 - 281
[28] Facile One-Pot Microwave-Assisted Synthesis and Ultrafast Spectroscopic Characterization of Nitrogen-Sulfur-Codoped Carbon Quantum Dots
Venkatesh, Yeduru
Wadepalli, Sadashiv
Bangal, Prakriti Ranjan
Naidu, Parimi Venkata Subrahmanyam
Rao, Podilapu Atchutha
LUMINESCENCE, 2025, 40 (02)
[29] A Nitrogen-Assisted One-Pot Heteroaryl Ketone Synthesis from Carboxylic Acids and Heteroaryl Halides
Demkiw, Krystyna
Araki, Hirofumi
Elliott, Eric L.
Franklin, Christopher L.
Fukuzumi, Yoonjoo
Hicks, Frederick
Hosoi, Kazushi
Hukui, Tadashi
Ishimaru, Yoichiro
O'Brien, Erin
Omori, Yoshimasa
Mineno, Masahiro
Mizufune, Hideya
Sawada, Naotaka
Sawai, Yasuhiro
Zhu, Lei
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (08) : 3447 - 3456
[30] One-pot synthesis of 1,2,4-oxadiazoles from chalcogen amino acid derivatives under microwave irradiation
Wolf, Lucas
Mayer, Joao C. P.
Quoos, Natalia
Sauer, Andre C.
Schwab, Ricardo S.
Rodrigues, Oscar E. D.
Dornelles, Luciano
TETRAHEDRON, 2021, 91

← 1 2 3 4 5 →