A mild and efficient method for the preparation of n-tosyl amides and lactams |
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| Affiliation: | 1. State Key Laboratory for Enhanced Oil Recovery, Beijing 100083, China;2. Research Institute of Petroleum Exploration and Development, PetroChina, China;1. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Mahidol University, 447 Sri-Ayudya Road, Bangkok 10400, Thailand;2. Division of Pathogenic Biochemistry, Institute of Natural Medicine, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan;3. Center of Excellence for Innovation in Drug Design and Discovery, Faculty of Pharmacy, Mahidol University, 447 Sri-Ayudya Road, Bangkok 10400, Thailand;1. Institute of Physiologically Active Compounds, Russian Academy of Sciences, 142432 Chernogolovka, Moscow Region, Russian Federation;2. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 119991 Moscow, Russian Federation;3. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation;4. L. Ya. Karpov Institute of Physical Chemistry, 105064 Moscow, Russian Federation;1. Department of Chemistry and Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Tsinghua University, Beijing 100084, China;2. Department of Chemistry/Institute of Polymers, Nanchang University, 999 Xuefu Avenue, Nanchang 330031, China |
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| Abstract: | N-tosyl amides and lactams can be prepared easily and under mild conditions by the inter- or intramolecular condensation of carboxylic acids and secondary sulfonamides. The coupling reagent used is dicyclohexyl-carbodiimide (DCC) in the presence of 4-pyrrolidinopyridine (4-PPY) and the reactions proceed readily, usually in high yield, at room temperature. |
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