The terminal alkyne was constructed in chlorin chromophore by Grignard reaction and oxidation to give chlorin 2 and 3, respectively. After deprotection the diketo chlorin 4 was obtained which was readily converted to the Zn-complex 5. Chlorin-enediyne dyads 6 fused with heterocyclic ring was synthesized by a palladium-catalyzed coupling reaction with 2-(1-hexynyl)-3-chlorothiophene.
Isochrom anone-4 1 was used as a starting m aterial and Pfitzinger reaction was carried out by condensation w ith isatin 2 to give 7-carboxyl group isochrom ano[4,3-b] qu inoline 3 whose ester 4 was obtained by treatm ent w ith d iazom ethane.A fter the G rignard reaction of 4 w ith m ethylm agnesium brom ide the m ethoxycarbonyl group was converted into the tertiary alcohol structure to generate isochrom an derivative 5.The dehydration of hydroxyl group at 7-position of 5 using TsOH as catalyst afforded dehydrated product 6.The structures of all these new compounds were characterized by elem ental analysis,IR and1H NMR spectra.
