酰基酰肼、氨基甲酸酯、氨基脲、氨基酸和伯胺亚单体制备杂二酮哌嗪的固相合成。
Solid-Phase Synthesis of Hybrid 2,5-Diketopiperazines Using Acylhydrazide, Carbazate, Semicarbazide, Amino Acid, and Primary Amine Submonomers.
机构信息
Department of Chemistry, School of Natural Sciences, Shiv Nadar University, Dadri, Uttar Pradesh 201314, India.
New Chemistry Unit, Jawaharlal Nehru Centre for Advanced Scientific Research (JNCASR), Jakkur, Bangalore 560064, India.
出版信息
J Org Chem. 2020 Mar 6;85(5):2927-2937. doi: 10.1021/acs.joc.9b02083. Epub 2020 Feb 11.
We report the solid-phase synthesis of ,'-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.
我们报告了，'-二（酰氨基）-2,5-二酮哌嗪的固相合成，这是一种基于酰腙的构象刚性 2,5-DKP 支架，具有外环 N-N 键。我们还表明，不同组合的酰腙、氨基甲酸酯、半卡巴肼、氨基酸和伯胺可以通过固相亚单位合成途径用于合成高度多样化的混合 DKP 分子。最后，我们表明，在 DKP 环的一个碳原子中引入一个甲基取代基，生成手性 daa 和混合-DKPs，而不会影响合成效率。
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