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The crystal and molecular structure of the 7‐ and 8‐chloro analogs of the 1‐azaphenoxathiin system are described. In contrast to previous compounds possessing antipsychotic type activity, the title compounds are both nearly planar, and demonstrate significant substituent location sensitivity, with the 7‐chloro analog exhibiting significant biologic activity while the 8‐chloro isomer is nearly devoid of activity. The relationship of these compounds to the isosterically related phenothiazines in terms of design and molecular geometry considerations is also described.

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The condensation of the disodium salt of 2‐mercapto‐3‐pyridinol with various ortho‐nitrohalo‐benzenes to yield a group of previously unreported 1‐azaphenoxathiins is described. The synthetic pathway and the substituent location on the products is unequivocably demonstrated by Fourier Transform1 3 C‐nmr. Preliminary pharmacologic evaluation of the title compounds as potential CNS depressant agents is also reported.

In an extension of recently reported syntheses of the I‐azaphenoxathiin nucleus as well as several 7‐substituted analogs, the synthesis of several 9‐substituted members of this series is now reported. In addition, the first 13C‐nmr spectral evidence of an interaction between a sulfur atom and the oxygen of an ortho‐nilro group which has been previously observed only in X‐ray erystallographic studies is also described. The possible consequences of this interaction on the reaction pathway leading to the cyclization of the 9‐substituted J‐azaphenoxathiin nucleus is also presented.