Regio- and Diastereoselective Synthesis of beta-Lactam-Triazole Hybrids via Passerini/CuAAC Sequence

作者：Alcaide Benito^*; Almendros Pedro; Aragoncillo Cristina; Callejo Ricardo; Pilar Ruiz M; Rosario Torres M

来源：Journal of Organic Chemistry, 2012, 77(16): 6917-6928.

DOI：10.1021/jo301113g

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.

• 出版日期2012-8-17