ORGN 170 |
Preparation and crystallographic characterization of fused-ring 4H-thiadiazines
| Piotr Kaszynski1, Jozef Zienkiewicz1, and Victor G. Young Jr.2. (1) Department of Chemistry, Vanderbilt University, Nashville, TN 37235, (2) Chemistry Department, University of Minnesota, 207 Pleasant St. S.E, Minneapolis, MN 55455 |
Four bicyclic [1,2,4]-4H-thiadiazines 1a-1d were prepared by oxidative cyclization of N-(2-propylthioaryl)benzamidines and subsequent thermal elimination of propene from the resulting S-propylsulfimines. The Ei mechanism was investigated using DFT methods. The elimination in the sulfilimines appear to be close in energy to the analogous elimination in sulfoxides. Crystal and molecular structures of three of the four thiadiazines were established by single crystal X-ray analysis and compared with theoretical models. The method for the synthesis of 1 appears to be general, high yield and convenient, and it has been extended to more highly substituted derivatives of 1.  |
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