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