title: Versatile Protecting-Group Free Tetrazolomethane Amine Synthesis by Ugi Reaction.
abstract: The use of ammonia in the Ugi reaction is often problematic due to low yields and multiple side reactions. Here, we report the use of ammonia in the tetrazole Ugi variation providing a clean, good-to-high yielding reaction, especially with ketones as oxo components. The scope and limitations of this reaction and a structure-reactivity relationship are provided by performing >85 reactions. The primary amine component of the α-amino tetrazole is a versatile starting material for further reactions.
authors: University of Groningen , Department of Drug Design, A. Deusinglaan 1, 9713 AV Groningen, The Netherlands.
authors: Pravin
authors: P
authors: Patil
authors: University of Groningen , Department of Drug Design, A. Deusinglaan 1, 9713 AV Groningen, The Netherlands.
authors: Michel
authors: M
authors: de Haan
authors: Jagiellonian University , Faculty of Chemistry, Department of Crystal Chemistry and Crystal Physics, Biocrystallography Group, Ingardena 3, 30-060 Kraków, Poland.
authors: Katarzyna
authors: K
authors: Kurpiewska
authors: Jagiellonian University , Faculty of Chemistry, Department of Crystal Chemistry and Crystal Physics, Biocrystallography Group, Ingardena 3, 30-060 Kraków, Poland.
authors: Justyna
authors: J
authors: Kalinowska-Tłuścik
authors: University of Groningen , Department of Drug Design, A. Deusinglaan 1, 9713 AV Groningen, The Netherlands.
authors: Alexander
authors: A
authors: Dömling
mesh_terms: D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D000641:Ammonia / Q000138:chemical synthesis / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques / Q000379:methods; D018360:Crystallography, X-Ray; D008697:Methane / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D013777:Tetrazoles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000588:Amines; D013777:Tetrazoles; D000641:Ammonia; D008697:Methane
keywords: Ugi reaction; aminomethyltetrazole; ammonia; multicomponent reaction