Thiazole Synthesis by Cyclocondensation of 1-Alkynyl(phenyl)-λ3-iodanes with Thioureas and Thioamides†
Kazunori Miyamoto
Faculty of Pharmaceutical Sciences, University of Tokushima, 1-78 Shomachi, Tokushima 770-8505, Japan, Fax: (+81) 88-633-9504
Search for more papers by this authorYoshio Nishi Dr.
Faculty of Pharmaceutical Sciences, University of Tokushima, 1-78 Shomachi, Tokushima 770-8505, Japan, Fax: (+81) 88-633-9504
Search for more papers by this authorMasahito Ochiai Prof.
Faculty of Pharmaceutical Sciences, University of Tokushima, 1-78 Shomachi, Tokushima 770-8505, Japan, Fax: (+81) 88-633-9504
Search for more papers by this authorKazunori Miyamoto
Faculty of Pharmaceutical Sciences, University of Tokushima, 1-78 Shomachi, Tokushima 770-8505, Japan, Fax: (+81) 88-633-9504
Search for more papers by this authorYoshio Nishi Dr.
Faculty of Pharmaceutical Sciences, University of Tokushima, 1-78 Shomachi, Tokushima 770-8505, Japan, Fax: (+81) 88-633-9504
Search for more papers by this authorMasahito Ochiai Prof.
Faculty of Pharmaceutical Sciences, University of Tokushima, 1-78 Shomachi, Tokushima 770-8505, Japan, Fax: (+81) 88-633-9504
Search for more papers by this authorWe gratefully acknowledge the Ministry of Education, Culture, Sports, Science, and Technology of Japan for financial support in the form of a grant.
Graphical Abstract
Die Isolierung und intramolekulare Cyclisierung von (S)-(1-Alkinyl)isothiouronium- und (S)-(1-Alkinyl)thiobenzimidoniumsalzen lassen Schlüsse auf den Mechanismus der Eintopfsynthese von 2,4-disubstituierten Thiazolen zu (siehe Schema; Ms=Methansulfonyl): Michael-Addition von Schwefelnucleophilen an hypervalente Iodane und anschließende 1,2-Umlagerung von Sulfenylgruppen in den gebildeten Alkylidencarbenen.
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