Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 5, Pages 2927-2937Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b02083
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- Science and Engineering Research Board (SERB), Department of Science and Technology (DST), Government of India [ECR/2015/000337]
- Shiv Nadar University (SNU)
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We 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.
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