'Atypical Ugi' tetrazoles

Eman M M Abdelraheem, Imogen Goodwin, Shabnam Shaabani, Michel P de Haan, Katarzyna Kurpiewska, Justyna Kalinowska-Tłuścik, Alexander Dömling*

*Bijbehorende auteur voor dit werk

OnderzoeksoutputAcademicpeer review

3 Citaten (Scopus)
70 Downloads (Pure)

Samenvatting

Amino acid-derived isocyano amides together with TMSN3, oxocomponents and 1° or 2° amines are common substrates in the Ugi tetrazole reaction. We surprisingly found that combining these substrates gives two different constitutional isomeric Ugi products A and B. A is the expected classical Ugi product whereas B is an isomeric product ('atypical Ugi') of the same molecular weight with the tetrazole heterocycle migrated to a different position. We synthesized, separated and characterized 22 different isomorphic examples of the two constitutional isomers of the Ugi reaction to unambiguously prove the formation of A and B. Mechanistic studies resulted in a proposed mechanism for the concomitant formation of A and B.

Originele taal-2English
Pagina's (van-tot)1799-1802
Aantal pagina's4
TijdschriftChemical communications (Cambridge, England)
Volume56
Nummer van het tijdschrift12
Vroegere onlinedatum17-jan.-2020
DOI's
StatusPublished - 11-feb.-2020

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