Two Cycles with One Catch: Hydrazine in Ugi 4-CR and Its Postcyclizations

Yuanze Wang, Pravin Patil, Katarzyna Kurpiewska, Justyna Kalinowska-Tluscik, Alexander Domling*

*Bijbehorende auteur voor dit werk

OnderzoeksoutputAcademicpeer review

13 Citaten (Scopus)
220 Downloads (Pure)

Samenvatting

Isocyanide-based multicomponent reactions (IMCR) are by far the most versatile reactions that can construct relatively complex molecules by one-pot synthesis. More importantly, the development of post IMCR modifications significantly improves the scaffold's diversity. Here, we describe the use of N-Boc protected hydrazine together with a-amino acid derived isocyanides in the Ugi tetrazole reaction and its post cyclization under both acidic and basic conditions. The cyclization in acidic conditions was conducted in a one pot fashion, which give 7-aminotetrazolopyrazinone (6) and tetrazolotriazepinone (7) cyclic products. The post cyclization under basic condition could selectively afford Boc-protected 7-aminotetrazolopyrazinone (8) products in yield of 38-87%.

Originele taal-2English
Pagina's (van-tot)193-198
Aantal pagina's6
TijdschriftAcs combinatorial science
Volume19
Nummer van het tijdschrift3
DOI's
StatusPublished - 13-mrt-2017

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