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A series of 2-amino-4-aryl-4H-1-benzothieno[3,2-b]pyran-3-carboxylates and 2-amino-4-aryl-3-cyano-4H-1-benzothieno[3,2-b]pyrans has been synthesized through Michael addition of (Z)-2-arylidenebenzo[b]thiophen-3(2H)-ones with active methylene compounds, such as ethyl cyanoacetate and malononitrile. The reaction was carried out in ethanol, in the presence of piperidine as a basic catalyst. The structures of the prepared compounds were determined by spectroscopic methods: 1 H-NMR, 13 C-NMR and confirmed by single crystal X-Ray diffraction.

The title compound C20H20O2, has the exocyclic C=C double bond in an E configuration. The two benzene rings form a dihedral angle of 72.92 (6)°.

We report herein the design and synthesis of 17 new spiroheterocycles 10-26, on the basis of two hypothetical pharmacophore structures designed to interact with both of Mycobacterium tuberculosis bacteria and HIV-1 virus. The in vitro biological evaluation of these compounds allowed us to point out seven new potential non-nucleoside hits, with MIC values in the range of 6.25 µg/mL and two new potential anti-HIV-1 inhibitors .