A new, easy access to the 6-aminoperhydro-1,4-diazepine scaffold under ultrasound and microwave irradiation

Alessandro Barge, Silvia Füzerová, Dharita Upadhyaya, Davide Garella, Silvio Aime, Lorenzo Tei, Giancarlo Cravotto

Risultato della ricerca: Contributo su rivistaArticolo in rivistapeer review

Abstract

A novel, efficient, and rapid synthesis of the 6-aminoperhydro-1,4- diazepine scaffold is reported. It was promoted by microwave or sequential ultrasound/microwave irradiation under solvent-free conditions or in solution. Protected ethylenediamine derivatives and N-Boc-serinol dimesylate underwent rapid cyclization to give 6-aminoperhydro-1,4-diazepine derivatives in excellent yields and with high selectivity, whereas the same reaction failed or gave negligible yields under conventional heating. Cesium or potassium ions catalyzed the ring closure by coordinating the sulfon-amide groups. All relevant work reported to date in the literature mostly concern about the syntheses of either 1H-tetrahydro-1,4-diazepine-2,5-dione or substituted 1,4-benzodiazepines, while the few published procedures for the preparation of 6-aminoperhydro-1,4- diazepines involved several steps, required long reaction times and afforded low yields. By the present method, access to 6-aminoperhydro-1,4-diazepines becomes much easier and faster.

Lingua originaleInglese
Numero di articoloT19307SS
pagine (da-a)1879-1882
Numero di pagine4
RivistaSynthesis
Numero di pubblicazione12
DOI
Stato di pubblicazionePubblicato - 17 giu 2008

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