Syntheses of 2,3‐dimethyl‐4H‐furo[3,2‐c]coumarin and 3‐phenyl‐4H‐furo[3,2‐c]coumarin as angular furocoumarins were carried out through Williamson reaction of 4‐hydroxycoumarin with α‐haloketones followed by cyclization. Photooxygenation of the synthesized furocoumarin derivatives was performed and the photoproducts were isolated and characterized. The affinity of 2,3‐dimethyl‐4H‐furo[3,2‐c]coumarin towards DNA and the antibacterial activity were evaluated and compared with 8‐methoxypsoralen (8‐MOP).
Synthesis of linear and angular furocoumarins with new skeleton structure of potential photobiological feature interest was carried out through Williamson reaction of hydroxycoumarins with 3‐chloro‐2‐butanone followed by cyclization with polyphosphoric acid or by heating in a strongly alkaline solution. The photooxygenation reactions of synthesized furocoumarins were performed in chloroform and in the presence of tetraphenylporphyrin as singlet oxygen sensitizer (1O2). The photooxygenation reactions afforded the photocleaved product through [2 + 2] cycloaddition and the photooxygenated products through ene reaction and [4 + 2] cycloaddition. The photoproducts were isolated and fully characterized by spectral analyses.
Reactions of cyano olefins with (i) enamino imides afforded novel pyrrolo[3,4‐b]pyridines; (ii) enamino esters afforded new 1,4‐dihydropyridines; and (iii) bisenamino ester afforded new 1,1′‐(1,4‐phenylene)bis(1,4‐dihydropyridine). The new derivatives are planned as suggested drug candidates.
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