dc.identifier.citation |
Tutar, A., Erenler, R., & Biellmann, J. F. (2013). Synthesis of 8-substituted 4, 4-difluoro-4-bora-3a, 4a-diaza-s-indacene Dyes (BODIPY). J Chem Soc Pak, 35, 1197-201. |
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dc.description.abstract |
4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dyes are important in synthetic and applied chemistry. The reaction of pyrrolomethane 1 with acetyl chloride and boron trifluoride etherate in the presence of triethylamine afforded the 4,4-Difluoro-3,5,8-trimethyl-4-bora-3a,4a-diaza-s-indacene 2a. When benzoylchloride and chloroacetyl chloride were used, phenyl 2b and chloromethyl 2c derivatives formed. The treatment of pyrrolomethane 1 with 3- (phenylthio)propanal 3 in the presence of ytterbium (III) trifluoromethanesulfonate hydrate in catalitic amount yielded the 5-(2-thiophenyl ethane)-1,9-dimethyldipyrromethane 4, which was reacted with DDQ and boron trifluoride etherate in the presence of triethylamine formed 8-(2-thiophenylethan) 4,4-difluoro-3,5dimethyl-4-bora-3a,4a-diaza-3-indacene 5. The oxidation of 8-(thiomethyl) 4,4-difluoro-3,5-dimethyl-4-bora-3a,4a-diaza-s-indacene 6 with m-CPBA gave methylsulfonyl product 7. Bromination of 4,4-difluoro-3,5,8-trimethyl-4-bora-3a,4a-diaza-s-indacene 2a yielded 1,2,6,7-tetrabromo-4,4-difluoro-3,5,8-trimethyl-4-bora-3a,4a-diaza-s-indacene 8. |
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