Synthesis of New Fluorine Substituted Heterocyclic Nitrogen Systems Derived from p-Aminosalicylic Acid as Antimycobacterial Agents

Some new fluorine substituted heterocyclic nitrogen systems 2–17 have been synthesized from ring closure reactions of substituted p ‐amino salicylic acids (PAS). The Schiffs base of PAS was cyclized with chloroacetyl chloride and mercaptoacetic acid to give azetidinone 2 , thiazolidinone 3 , and spiro‐fluoroindolothiazoline‐dione 10 . However, PAS when reacted directly with 4‐fluorobenzoyl chloride and 5‐oxazolinone yielded derivatives 4 , 5 , and 7 . Aminomethylation of PAS using formaldehyde and piperidine or piperazine formed N‐alkyl and N,N′‐dialkyl derivatives ( 11 and 12 respectively) upon fluorinated benzoylation gave compounds 13 and 14 . Similarly, treatment of PAS with thiosemicarbazide 15 and subsequent cyclization with diethyl oxalate yielded the fluorinated heterocycle 17 . The structures of the fluorinated heterocyclic systems have been established on the basis of elemental analysis, 1 H NMR, 13 C NMR, and MS spectral data. Some of the targets exhibited a high inhibition towards Mycobacterium strain with favorable log P values.

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