• Journal of the Korean Chemical Society
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• v.54 no.3
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• pp.350-353
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• 2010

• Bulletin of the Korean Chemical Society
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• v.32 no.3
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• pp.909-914
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• 2011

An improved convergent and economical method has been developed for the synthesis of erlotinib, a 4-anilinoquinazoline and an EGFR-tyrosine kinase inhibitor for treatment of non-small-cell lung cancer. The final two steps for the formation of this 4-anilinoquinazoline from suitable 2-aminobenzonitrile intermediate and 3-ethynylaniline were modified and were performed in a simple one-pot reaction. The ring-closing mechanism for the formation of erlotinib from the suitable formamidine intermediate and 3-ethynylaniline was investigated and determined to proceed via the formation of phenyl benzamidine intermediate rather than involving Dimroth rearrangement reported earlier. The new benzamidine intermediate was isolated for the first time and characterized.

• Journal of the Korean Chemical Society
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• v.54 no.6
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• pp.841-843
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• 2010

• Journal of the Korean Chemical Society
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• v.55 no.2
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• pp.218-229
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• 2011

We have involved the imine compound 1 in condensations with various nitrogenous reagents including hydrazine hydrate to construct differently substituted pyrimidines. One of the pyrimidines so obtained was further subjected to interactions with different reagents such as propionic acid, formic acid, ethyl chloroformate, acdetic anhydride, carbon disulphide, cyanogene bromide, triflauroacetic acid and ethyl chloroacetate which resulted in the formation of annulated heterocyclic systems as pairs of isomers in most cases as a result of Dimroth-type rearrangement.