BIOMAT Database Logo BIOMAT Database Logo

Multi-Gram Synthesis of Enantiopure 1,5-Disubstituted Tetrazoles Via Ugi-Azide 3-Component Reaction. 2018

Pietro Capurro, and Lisa Moni, and Andrea Galatini, and Christian Mang, and Andrea Basso
Dipartimento di Chimica e Chimica Industriale, Università degli Studi di Genova, Via Dodecaneso 31, 16146 Genoa, Italy. pietro.capurro@outlook.it.

Tetrazoles have been widely studied for their biological properties. An efficient route for large-scale synthesis of 1,5-disubstituted tetrazoles (1,5-DTs) is presented. The strategy exploits a reductive approach to synthetize a cyclic chiral imine substrate which is then converted into the target product through an Ugi-azide three-component reaction (UA-3CR). The final products are equipped with additional functionalities which can be further elaborated for the generation of combinatorial libraries of enantiopure heterocycles.

UI MeSH Term Description Entries
D007097 Imines Organic compounds containing a carbon-nitrogen double bond where a NITROGEN atom can be attached to HYDROGEN or an alkyl or aryl group. Imine
D002384 Catalysis The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction. Catalyses
D002855 Chromatography, Thin Layer Chromatography on thin layers of adsorbents rather than in columns. The adsorbent can be alumina, silica gel, silicates, charcoals, or cellulose. (McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed) Chromatography, Thin-Layer,Thin Layer Chromatography,Chromatographies, Thin Layer,Chromatographies, Thin-Layer,Thin Layer Chromatographies,Thin-Layer Chromatographies,Thin-Layer Chromatography
D001386 Azides Organic or inorganic compounds that contain the -N3 group. Azide
D013777 Tetrazoles
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular

Related Publications

Pietro Capurro, and Lisa Moni, and Andrea Galatini, and Christian Mang, and Andrea Basso
Consecutive hydrazino-Ugi-azide reactions: synthesis of acylhydrazines bearing 1,5-disubstituted tetrazoles.
January 2017, Beilstein journal of organic chemistry,
Pietro Capurro, and Lisa Moni, and Andrea Galatini, and Christian Mang, and Andrea Basso
Synthesis of N-heterocycles containing 1,5-disubstituted-1H-tetrazole via post-Ugi-azide reaction.
August 2020, Molecular diversity,
Pietro Capurro, and Lisa Moni, and Andrea Galatini, and Christian Mang, and Andrea Basso
Synthesis of novel bis-1,5-disubstituted-1H-tetrazoles by an efficient catalyst-free Ugi-azide repetitive process.
January 2015, Molecules (Basel, Switzerland),
Pietro Capurro, and Lisa Moni, and Andrea Galatini, and Christian Mang, and Andrea Basso
Facile synthesis of 1,5-disubstituted tetrazoles by reacting a ruthenium acetylide complex with trimethylsilyl azide.
August 2019, Dalton transactions (Cambridge, England : 2003),
Pietro Capurro, and Lisa Moni, and Andrea Galatini, and Christian Mang, and Andrea Basso
A three-component reaction of C,N-cyclic N'-acyl azomethine imines, isocyanides, and azide compounds: effective synthesis of 1,5-disubstituted tetrazoles with tetrahydroisoquinoline skeletons.
April 2013, Organic & biomolecular chemistry,
Pietro Capurro, and Lisa Moni, and Andrea Galatini, and Christian Mang, and Andrea Basso
Library-to-Library Synthesis of Highly Substituted α-Aminomethyl Tetrazoles via Ugi Reaction.
February 2018, ACS combinatorial science,
Pietro Capurro, and Lisa Moni, and Andrea Galatini, and Christian Mang, and Andrea Basso
Synthesis of 2-Tetrazolyl-Substituted 3-Acylpyrroles via a Sequential Ugi-Azide/Ag-Catalyzed Oxidative Cycloisomerization Reaction.
October 2018, The Journal of organic chemistry,
Pietro Capurro, and Lisa Moni, and Andrea Galatini, and Christian Mang, and Andrea Basso
Improved synthesis of 15-deoxyspergualin analogs using the Ugi multi-component reaction.
May 2011, Bioorganic & medicinal chemistry letters,
Pietro Capurro, and Lisa Moni, and Andrea Galatini, and Christian Mang, and Andrea Basso
Polymacrocycles Derived via Ugi Multi-Component Reactions.
February 2019, Macromolecular rapid communications,
Pietro Capurro, and Lisa Moni, and Andrea Galatini, and Christian Mang, and Andrea Basso
Copper(i) catalyzed oxidative hydrolysis of Ugi 3-component and Ugi-azide reaction products towards 2° α-ketoamides and α-ketotetrazoles.
July 2017, Organic & biomolecular chemistry,
Copied contents to your clipboard!