Reaction of isocyanates with 2‐phenyliminotetrahydro‐1,3‐thiazines and oxazines

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Abstract
It has been found that the reaction of isocyanates with 2‐phenyliminotetrahydro‐1,3‐thiazines and oxazines 3–8 occurs at the ring nitrogen to give the endo carbamoylated compound first, and then the carbamoyl group migrates to the exo nitrogen with differing rates depending upon the structure of the thiazines or the oxazines. Though the carbamoylated thiazines (both endo and exo) were found to exist in equilibrium with the isocyanate and the thiazine in solution, crossover experiments showed that the rearrangement proceeded by an intramolecular mechanism.

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