Journal
ACS COMBINATORIAL SCIENCE
Volume 19, Issue 3, Pages 193-198Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscombsci.7b00009
Keywords
isocyanide-based multicomponent reactions; hydrazine; post cyclization; tetrazole; one-pot synthesis; scaffolds diversity; European Lead Factory
Funding
- NIH [2R01GM097082-05]
- Innovative Medicines Initiative [115489]
- European Union [675555]
- European Regional Development Fund in the framework of the Polish Innovation Economy Operational Program [POIG.02.01.00-12-023/08]
- China Scholarship Council
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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%.
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