jo9b02083_si_003.cif (127.03 kB)
Solid-Phase Synthesis of Hybrid 2,5-Diketopiperazines Using Acylhydrazide, Carbazate, Semicarbazide, Amino Acid, and Primary Amine Submonomers
dataset
posted on 2020-02-11, 13:09 authored by Abdur Rahim, Biswajit Sahariah, Kalpita Baruah, Jugal Kishore Rai Deka, Bani Kanta SarmaWe
report the solid-phase synthesis of N,N′-di(acylamino)-2,5-diketopiperazine, an acylhydrazide-based
conformationally rigid 2,5-DKP scaffold having exocyclic N–N
bonds. We also show that different combinations of acylhydrazides,
carbazates, semicarbazides, amino acids, and primary amines can be
used to synthesize a highly diverse collection of hybrid DKP molecules
via the solid-phase submonomer synthesis route. Finally, we show incorporation
of a methyl substituent in one of the carbon atoms of the DKP ring
to generate chiral daa- and hybrid-DKPs without compromising the synthetic
efficiency.