Online citations, reference lists, and bibliographies.
← Back to Search

α-Nitro Ketone Synthesis Using N-Acylbenzotriazoles

A. Katritzky, A. Abdel-Fattah, A. V. Gromova, R. Witek, P. Steel
Published 2005 · Chemistry

Cite This
Download PDF
Analyze on Scholarcy
Share
Readily available N-acylbenzotriazoles 2a−l (derived from a variety of aliphatic, (hetero)aromatic, and N-protected α-amino carboxylic acids) smoothly convert primary 3a−c and α-functionalized primary nitroalkanes 3d into the corresponding α-nitro ketones 5a−p in yields of 39−86% (average 63%).



This paper is referenced by
10.1016/J.TET.2009.02.070
Convenient synthesis of C-terminal di- and tri-peptide amides from N-protected dipeptidoylbenzotriazoles
I. Celik (2009)
10.1002/CHIN.200612088
α-Nitro Ketone Synthesis Using N-Acylbenzotriazoles.
A. R. Katritzky (2006)
10.3762/bjoc.8.220
Engineering of indole-based tethered biheterocyclic alkaloid meridianin into β-carboline-derived tetracyclic polyheterocycles via amino functionalization/6-endo cationic π-cyclization
P. K. Agarwal (2012)
10.1021/acsomega.9b00343
Silicon Industry Waste Polymethylhydrosiloxane-Mediated Benzotriazole Ring Cleavage: A Practical and Green Synthesis of Diverse Benzothiazoles
Mangal S. Yadav (2019)
10.1016/j.tet.2020.131078
Synthesis of 1-(2-bromo-1-arylethyl)-1H-benzotriazoles via NBS promoted addition of 1H-benzotriazole to alkene: Relevance in benzotriazole ring cleavage
M. Singh (2020)
10.1039/c1ob06260c
Domino reactions for the synthesis of various α-substituted nitro alkenes.
S. Fioravanti (2012)
10.1039/B712734K
Rapid C-carboxylation of nitro[(11)C]methane for the synthesis of ethyl nitro[2-(11)C]acetate.
K. Kato (2008)
10.1007/s00706-014-1408-1
Facile synthesis of N-acylbenzotriazoles from carboxylic acids mediated by 2,4,6-trichloro-1,3,5-triazine and triethylamine
Sirawit Wet-osot (2015)
10.1016/B978-008044992-0.00501-0
5.01 1,2,3-Triazoles
S. Rachwał (2008)
10.1016/J.TETLET.2019.04.030
Simple one pot synthesis of ketone from carboxylic acid using DCC as an activator
H. Mekonnen (2019)
10.1021/acs.joc.6b02704
Organocatalytic Insertion of Isatins into Aryl Difluoronitromethyl Ketones.
Ransheng Ding (2017)
10.1016/J.TET.2012.05.055
Synthesis of trisubstituted isoxazoles via in situ trapping strategy from α-nitro carbonyl compounds and methyl ketones or terminal aryl alkenes
Y. Yang (2012)
10.2174/1385272823666190820113718
Comprehension of the α-Arylation of Nitroalkanes
P. F. Zheng (2019)
10.1016/j.ejmech.2010.04.040
Chemistry around imidazopyrazine and ibuprofen: discovery of novel fatty acid amide hydrolase (FAAH) inhibitors.
Frédéric De Wael (2010)
10.1021/ol5014153
General Route for Preparing β-Nitrocarbonyl Compounds Using Copper Thermal Redox Catalysis
Amber A. S. Gietter (2014)
10.1021/jo2009752
Organocatalytic asymmetric conjugate addition and cascade acyl transfer reaction of α-nitroketones.
R. Lu (2011)
10.1055/S-0037-1611724
Trichloroisocyanuric Acid Mediated High-Yielding Synthesis of N-Acylbenzotriazoles under Mild Reaction Conditions
M. Singh (2019)
10.1055/S-0037-1610277
An Improved N-Acylation of 1H-Benzotriazole Using 2,2′-Dipyridyl­di­sulfide and Triphenylphosphine
Anoop S. Singh (2019)
10.1002/anie.201904034
Development of a Chemo- and Enantioselective Pd-Catalyzed Decarboxylative Asymmetric Allylic Alkylation of α-Nitroesters.
B. Trost (2019)
10.1002/ADSC.201800163
Synthetic Procedures for the Preparation of Nitroalkanes
R. Ballini (2018)
10.1007/s11426-019-9586-3
Amides as surrogates of aldehydes for C-C bond formation: amide-based direct Knoevenagel-type condensation reaction and related reactions
W. Ou (2019)
10.1007/7081_2014_121
1,2,3-Triazoles Fused to Aromatic Rings
B. Abarca (2014)
10.1002/EJOC.201403076
Acyloxyphosphonium versus Aminophosphonium Intermediates: Application to the Synthesis of N‐Acylbenzotriazoles
Chuthamat Duangkamol (2014)
10.1039/c5cc00123d
Palladium-catalysed carbonylative α-arylation of nitromethane.
Zhong Lian (2015)
Semantic Scholar Logo Some data provided by SemanticScholar