Efficient Synthesis of Biomass-Derived N-Substituted 2-Hydroxymethyl-5-Methyl-Pyrroles in Two Steps from 5-Hydroxymethylfurfural

被引:24
作者
Wozniak, Bartosz [1 ]
Li, Yuehui [2 ]
Hinze, Sandra [1 ]
Tin, Sergey [1 ]
de Vries, Johannes G. [1 ]
机构
[1] Univ Rostock, Leibniz Inst Katalyse, Albert Einstein Str 29a, D-18059 Rostock, Germany
[2] Chinese Acad Sci, State Key Lab Oxo Synth & Select Oxidat, Suzhou Res Inst LICP, LICP, Lanzhou 730000, Gansu, Peoples R China
关键词
Pyrroles; Paal-Knorr synthesis; Heterocycles; Cyclization; Renewable resources; PAAL-KNORR REACTION; CATALYTIC CONVERSION; PYRROLE; LIGANDS; DERIVATIVES; COMPLEXES;
D O I
10.1002/ejoc.201800171
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient two-step synthesis for the conversion of biomass-derived 5-hydroxymethyl-furfural (HMF) to a variety of N-substituted 2-hydroxymethyl-5-methylpyrroles was developed. In the first step, 1-hydroxyhexane-2,5-dione (HHD) was obtained by hydrogenation of HMF and thereafter used in a Paal-Knorr reaction with a range of amines in the absence of catalyst at room temperature. The reaction could potentially be used as a click reaction.
引用
收藏
页码:2009 / 2012
页数:4
相关论文
共 46 条
[1]   Mechanism of the Paal-Knorr reaction: the importance of water mediated hemialcohol pathway [J].
Abbat, Sheenu ;
Dhaked, Devendra ;
Arfeen, Minhajul ;
Bharatam, Prasad V. .
RSC ADVANCES, 2015, 5 (107) :88353-88366
[2]  
Anastas P., 1998, GREEN CHEM THEORY PR
[3]  
Anderson CE, 2006, DALTON T, P5362, DOI 10.1039/b611652c
[4]  
[Anonymous], ANGEW CHEM
[5]  
[Anonymous], ANGEW CHEM
[6]   Discovery of a Novel Pyrrole Derivative 1-[5-(2-Fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]-N-methylmethanamine Fumarate (TAK-438) as a Potassium-Competitive Acid Blocker (P-CAB) [J].
Arikawa, Yasuyoshi ;
Nishida, Haruyulci ;
Kurasawa, Osamu ;
Hasuoka, Atsushi ;
Hirase, Keizo ;
Inatomi, Nobuhiro ;
Hori, Yasunobu ;
Matsukawa, Jun ;
Imanishi, Akio ;
Kondo, Mitsuyo ;
Tarui, Naoki ;
Hamada, Teruki ;
Takagi, Terufumi ;
Takeuchi, Toshiyuki ;
Kajino, Masahiro .
JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (09) :4446-4456
[7]   Organic synthesis via magnetic attraction: benign and sustainable protocols using magnetic nanoferrites [J].
Baig, R. B. Nasir ;
Varma, Rajender S. .
GREEN CHEMISTRY, 2013, 15 (02) :398-417
[8]   Synthesis, Structure, and Complexation Properties of Partially and Completely Reduced meso-Octamethylporphyrinogens (Calix[4]pyrroles) [J].
Blangy, Valeria ;
Heiss, Christoph ;
Khlebnikov, Vsevolod ;
Letondor, Christophe ;
Stoeckli-Evans, Helen ;
Neier, Reinhard .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (09) :1688-1691
[9]  
Buntara T., 2011, Angewandte Chemie, V123, P7221, DOI DOI 10.1002/ANGE.201102156
[10]   Caprolactam from Renewable Resources: Catalytic Conversion of 5-Hydroxymethylfurfural into Caprolactone [J].
Buntara, Teddy ;
Noel, Sebastien ;
Phua, Pim Huat ;
Melian-Cabrera, Ignacio ;
de Vries, Johannes G. ;
Heeres, Hero J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (31) :7083-7087