Abstract
Abstract This Letter describes novel methodology for the rapid assembly of unprecedented and likely biologically relevant imidazo-tetrazolodiazepinones. The product of a TMSN3-Ugi multi-component reaction is treated with an excess of isocyanate to generate 1,5-disubstituted tetrazolo-hydantoins functionalized with an internal-masked amino nucleophile previously introduced by the isocyanide input. Final products are obtained in good overall yields after microwave irradiation of the tetrazolo-hydantoin in acidic media. This methodology allows the production of complex polycyclic compounds in a mere three synthetic steps.
Original language | English (US) |
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Article number | 46572 |
Pages (from-to) | 5295-5298 |
Number of pages | 4 |
Journal | Tetrahedron Letters |
Volume | 56 |
Issue number | 38 |
DOIs | |
State | Published - Sep 16 2015 |
Keywords
- Diazepinone
- Hydantoin
- Multicomponent reaction
- Tetrazole
- UDC
- Ugi reaction
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry