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Synthesis of 8-substituted 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene dyes (BODIPY)
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نویسنده
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tutar a. ,erenler r. ,biellmann j.-f.
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منبع
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journal of the chemical society of pakistan - 2013 - دوره : 35 - شماره : 4 - صفحه:1197 -1201
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چکیده
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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,4adiaza- 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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آدرس
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institute of chemistry,academia sinica,taipei 115,taiwan,sakarya university,faculty of art and science,department of chemistry, Turkey, institute of chemistry,academia sinica,taipei 115,taiwan,gaziosmanpasa university,faculty of art and science,department of chemistry, Turkey, institute of chemistry,academia sinica,taipei 115,taiwan,national central university, Taiwan
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Authors
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