Although the preparation of substituted oxazoles starting from N-protected amino acids reacting with oxalyl chloride has been reported, the optimization, limitations, and advantages of this method has not been thoroughly explored. This investigation reports the effects of solvents, electronic factors, concentration of reagents, temperature, reaction times, and conjugation had on the synthesis of oxazoles starting from N-protected amino acids. It was also demonstrated that this synthesis can be used to easily introduce various substituents into positions 2, 4, and 5 of the ring, thereby obtaining a highly functionalized oxazole. An electron withdrawing p-NO2C6H5 group and the electron donating p-CH3OC6H5 group at position 2, a methyl or bromomethyl substituent at position 4, and an ester or amide functional group at position 5 are all well tolerated with oxazole yields as high as 87%.

Exploring the synthesis of oxazoles starting from amino acids treated with oxalyl chloride

2019 Fall National Meeting

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