Facile synthesis of macrocyclic tetrazoles by regioselective cycloalkylation of bistetrazoles with 2,5-dimethylhexane-2,5-diol in perchloric acid

Autor:	Sergei V. Voitekhovich, Pavel N. Gaponik, Alexander S. Lyakhov, Ludmila S. Ivashkevich
Rok vydání:	2012
Předmět:	Organic Chemistry Diol Regioselectivity Crystal structure Alkylation Biochemistry Medicinal chemistry Perchlorate chemistry.chemical_compound Acid catalysis chemistry Drug Discovery Organic chemistry Tetrazole Perchloric acid
Zdroj:	Tetrahedron Letters. 53:6111-6114
ISSN:	0040-4039
Popis:	Alkylation of 1,5-bis(tetrazol-5-yl)-3-oxapentane with 2,5-dimethylhexane-2,5-diol in 65% aqueous perchloric acid was found to proceed selectively on the N2 atoms of both tetrazole rings generating a 15-membered macrocycle with tetrazol-2,5-diyl moieties incorporated (yield ca. 80%). Under analogous alkylation conditions 1,5-bis(1-methyltetrazol-5-yl)-3-oxapentane undergoes quaternization resulting in a macrocyclic tetrazolium perchlorate containing two 1-methyltetrazolium-3,5-diyl units linked by 3-oxapentane-1,5-diyl and 2,5-dimethylhexane-2,5-diyl bridges. Crystal structures of the macrocyclic compounds obtained, determined by single crystal X-ray analysis, are described.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::761cd96a57e2bf1c122749eeba186f95 https://doi.org/10.1016/j.tetlet.2012.08.146 Zobrazit plný text záznamu Full Text from ScienceDirect