DOI: 10.1055/a-2899-9281 ISSN: 0039-7881
Decarboxylative Recyclization of 3-Isocyanatoisochroman-1-ones
Roman Y. Vasylyshyn, Bohdan A. Demydchuk, Vasyl S. Matiychuk, Oleg Lukin, Grygoriy A. Dolgonos, Svetlana Shishkina, Alexander Shivanyuk, Yevhen Karpun, Sergiy M. Kovalenko, Volodymyr FetyukhinA previously unknown decarboxylative recyclization of 3-isocyanato-isochroman-1-ones occurs at 200-220°C in PhOPh solution to afford a series of pharmacophoric isoquinolin-1(2H)-ones in 89-94% yield on a 4-8 gram scale. DFT-D calculations predict the exothermicity and entropic favorability of the rearrangement and suggest it’s possible mechanism