Oxazine synthesis

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The reaction was fine tuned with a base to afford the (Z)-4- (iodo-methylene)-2-aryl-4H-benzo[d]-[1,3]oxazines in the presence of I2 via 6-exo-dig iodocyclization with high stereo-, regioand chemoselectivity. Stereochemistry of Z-isomer was confirmed by 1H NMR, NOESY and ORTEP. The DFT calculations M06-2x/6-31G* also revealed that the Z-form is more stable than the E-form by 3.5 kcal mol−1. Iodine substituted molecules have many applications in synthetic chemistry. We have succeeded with Suzuki reaction, which has afforded the desired product in high yields.

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