Regio- and chemoselective addition of alkynyltin reagents to the 2-position of 3-acylpyridines activated by methyl chloroformate: selective synthesis of 2,3-disubstituted 1,2-dihydropyridines |
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| Institution: | 1. Department of Pharmaceutical Sciences and Experimental Therapeutics, College of Pharmacy, The University of Iowa, Iowa City, IA 52242, USA;2. Department of Pharmacology and Molecular Sciences, Johns Hopkins University School of Medicine, 725 North Wolfe St., Baltimore, MD 21205, USA;3. Department of Onocology, Johns Hopkins University School of Medicine, 725 North Wolfe St., Baltimore, MD 21205, USA;1. Vanderbilt Center for Neuroscience Drug Discovery, Vanderbilt University, Nashville, TN 37232, USA;2. Department of Pharmacology, Vanderbilt University, Nashville, TN 37232, USA;3. Bristol-Myers Squibb Co., Research and Development, 5 Research Parkway, Wallingford, CT 06492, USA;4. Department of Chemistry, Vanderbilt University, Nashville, TN 37232, USA;5. Vanderbilt Kennedy Center, Vanderbilt University Medical Center, Nashville, TN 37232, USA;1. Spectrophysics Research Laboratory, PG and Research Department of Physics, Arignar Anna Government Arts College, Cheyyar, 604407, Tamil Nadu, India;2. Interdisciplinary Institute of Indian System of Medicine, SRM University, Kattankulathur, Chennai, 603203, Tamil Nadu, India;3. Sophisticated Analytical Instrumentation Facility, St. Peter''s Institute of Higher Education and Research, St.Peters University, Avadi, Chennai, 600054, Tamil Nadu, India;1. Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhauri, Bhopal 462 066, Madhya Pradesh, India;2. Department of Chemistry, Indian Institute of Science Education and Research Berhampur, Berhampur 760 010, Odisha, India;1. Catalysis and Peptide Research Unit, University of KwaZulu-Natal, Durban, South Africa;2. AnSynth PTY LTD, Durban, South Africa;3. School of Chemistry and Physics, University of KwaZulu-Natal, Durban, South Africa;4. Department of Biological, Physical and Health Sciences, College of Arts and Sciences, Roosevelt University, Chicago, IL, USA |
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| Abstract: | Alkynyltin reagents add to the 2-position of 3-acylpyridines activated by methyl chloroformate regio- and chemoselectively to give 2,3-disubstituted 1,2-dihydropyridines, whereas alkynyl Grignard reagents suffer from a lack of regio- or chemoselectivity. |
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