A synthesis of succinimides and glutarimides from cyclic anhydrides |
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| Affiliation: | 1. Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia;2. Department of Medicinal Chemistry, Faculty of Pharmacy, University of Mansoura, Mansoura 35516, Egypt;3. Department of Organic Chemistry, Faculty of Pharmacy, Al-Azhar University, Cairo 11884, Egypt;4. University of Florence, Neurofarba Department, Sezione di Scienze farmaceutiche, Via Ugo Schiff 6, 50019 Sesto Fiorentino (Florence), Italy;1. Instituto de Polímeros e Compósitos/I3N, Universidade do Minho, 4800-058 Guimarães, Portugal;2. Centro de Química, Universidade do Minho, 4710-057 Braga, Portugal;3. Departamento de Informática, Centro ALGORITMI, Universidade do Minho, 4710-057 Braga, Portugal;4. Instituto Nacional del Carbón, INCAR-CSIC, Apartado 73, 33080 Oviedo, Spain;1. Key Laboratory of Structure-Based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, 103 Wenhua Road, Shenhe District, Shenyang 110016, China;2. Department of Pharmacology, Shenyang Pharmaceutical University, 103 Wenhua Road, Shenhe District, Shenyang 110016, China;3. Division of Hematology/Oncology, Department of Medicine, Beth Israel Deaconess Medical Center and Harvard Medical School, Boston, MA 02215, USA;1. Jiangsu Co-innovation Center for Prevention and Control of Important Animal Infectious Diseases and Zoonoses, Jiangsu Key Laboratory of Zoonosis, School of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, People’s Republic of China;2. College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, People’s Republic of China;1. Institute for Materials Chemistry and Engineering, Kyushu University, 6-1 Kasuga-koen, Kasuga City, Fukuoka 815-8580, Japan;2. Nissan Chemical Industries, Ltd, 2-10-1 Tsuboi Nishi, Funabashi, Chiba 274-8507, Japan |
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| Abstract: | The transformation of cyclic anhydrides to their corresponding imides involves a mild three-step sequence: (1) reaction with a primary amine, (2) conversion of the intermediate monoamide to an N-hydroxysuccinimidyl ester using N,N′-disuccinimidyl oxalate (DSO), and (3) cyclization by heating the NHS ester in trichloroethylene in the presence of 4-(dimethylamino)pyridine. |
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