A General Synthetic Route to Isomeric Pyrrolo[1,2- x][1,4]diazepinones

The Journal of Organic Chemistry
Elena Y ZelinaMaxim G Uchuskin

Abstract

A simple one-pot method for the synthesis of isomeric pyrrolo[1,2- x][1,4]diazepinones in reasonable yields was developed. The method is based on the condensation of readily available N-Boc amino acids with biomass-derived furans containing aminoalkyl groups followed by deprotection, furan ring opening, and Paal-Knorr cyclization. Using this approach, we synthesized pyrrolo[1,2- a][1,4]diazepin-3(2 H)-ones from furfurylamines and β-amino acids and pyrrolo[1,2- d][1,4]diazepin-4(5 H)-ones from 2-(2-furyl)ethylamines and α-amino acids. The cytotoxicity of the synthesized pyrrolodiazepinones was studied.

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Citations

Dec 6, 2019·Chemical Science·Anton S MakarovA Stephen K Hashmi
Apr 29, 2021·The Journal of Organic Chemistry·Shutao WangJinbao Xiang
May 6, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Roman O ShcherbakovMaxim G Uchuskin
Jul 8, 2021·The Journal of Organic Chemistry·Petrakis N ChalikidiVladimir T Abaev

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