期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 72, 期 21, 页码 7963-7967出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo701292h
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资金
- NCRR NIH HHS [C06 RR-16572] Funding Source: Medline
We recently developed a new class of oligomers that contain a-amino acid residues linked by 1,2,3-triazole groups [Angelo, N. G.; Arora, P. S. J. Am. Chem. Soc. 2005, 127, 17134-17135]. Synthesis of these oligomers involves an iterative sequence consisting of diazotransfer and Huisgen 1,3-dipolar cycloaddition steps. In this contribution, we describe an efficient one-pot, two-step sequence for the preparation of triazoles from the corresponding amino acid-derived amines and alkynes in solution. The one-pot sequence affords the desired products in significantly higher yields than our original method. We also outline a highly effective protocol for the synthesis of these triazole-based biomimetic oligomers on the solid phase. We find that amino acid derivatives and iterative formation of triazole rings require nontraditional reaction conditions for high yields.
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