期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 77, 期 16, 页码 6917-6928出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo301113g
关键词
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资金
- MICINN [CTQ2009-09318]
- Comunidad Autonoma de Madrid (CAM) [S2009/PPQ-1752]
- UCM-Santander [GR35/10-A]
- MEC
Passerini (P-3CR) and Passerini-Smiles reactions were investigated in azetidine-2,3-diones, affording the corresponding 3,3-disubstituted-beta-lactams with complete diastereoselectivity in high yields. The study has been carried out using different isocyanides, carboxylic acids, and phenols showing the scope of both reactions. In addition, the regioselective synthesis of highly functionalized beta-lactam-triazole hybrids has been developed via a Passerini/CuAAC sequence. Interestingly, the use of dialkynes/diazides or trialkynes/triazides as linkers in the CuAAC step has allowed the synthesis of C-2 and C-3 symmetric beta-lactam-triazole hybrids, respectively.
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