Bromination at C-5 of Pyrimidine and C-8 of Purine Nucleosides with 1,3-Dibromo-5,5-dimethylhydantoin.

نویسندگان

  • Ramanjaneyulu Rayala
  • Stanislaw F Wnuk
چکیده

Treatment of the protected and unprotected nucleosides with 1,3-dibromo-5,5- dimethylhydantoin in aprotic solvents such as CH(2)Cl(2), CH(3)CN, or DMF effected smooth bromination of uridine and cytidine derivatives at C-5 of pyrimidine rings as well as adenosine and guanosine derivatives at C-8 of purine rings. Addition of Lewis acids such as trimethylsilyl trifluoromethanesulfonate enhanced efficiency of bromination.

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

An efficient and facile methodology for bromination of pyrimidine and purine nucleosides with sodium monobromoisocyanurate (SMBI).

An efficient and facile strategy has been developed for bromination of nucleosides using sodium monobromoisocyanurate (SMBI). Our methodology demonstrates bromination at the C-5 position of pyrimidine nucleosides and the C-8 position of purine nucleosides. Unprotected and also several protected nucleosides were brominated in moderate to high yields following this procedure.

متن کامل

1,3-Dibromo-5,5-dimethylhydantoin: a versatile catalyst for synthesis of 3,3-bis(indolyl)oxindoles

A condensation of various isatins with indole derivatives has been carried out in the presence of 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) as catalyst at 50 °C in ethanol in order to form 3,3-bis(indolyl) oxindoles. The products were obtained within 20-90 min by 70-96% yields. The efficacy of the procedure has been confirmed by catalyzing the condensation reaction of pyrrole which was used as ...

متن کامل

1,3-Dibromo-5,5-dimethylhydantoin (DBH) as a cheap and efficient catalyst for the synthesis of polyhydroquinolines and 12-aryl-8,9,10,12-tetrahydro [a] xanthene-11-ones

1,3-Dibromo-5,5-dimethylhydantoin (DBH), as a cheap and commercially available reagent, is efficiently able to catalyze the synthesis of polyhydroquinoline derivatives and 12-aryl-8,9,10,12-tetrahydro[a] xanthene-11-ones via one-pot multi-component reactions. This novel synthetic method has the advantages of low cost and availability of the catalyst, short reaction times, high to excellent yiel...

متن کامل

Synthesis of 8-(1,2,3-triazol-1-yl)-7-deazapurine nucleosides by azide-alkyne click reactions and direct C-H bond functionalization.

Treatment of toyocamycin or sangivamycin with 1,3-dibromo-5,5-dimethylhydantoin in MeOH (r.t./30 min) gave 8-bromotoyocamycin and 8-bromosangivamycin in good yields. Nucleophilic aromatic substitution of 8-bromotoyocamycin with sodium azide provided novel 8-azidotoyocamycin. Strain promoted click reactions of the latter with cyclooctynes resulted in the formation of the 1,2,3-triazole products....

متن کامل

1,3-Dibromo-5,5-dimethylhydantoin (DBH) as a cheap and efficient catalyst for the synthesis of polyhydroquinolines and 12-aryl-8,9,10,12-tetrahydro [a] xanthene-11-ones

1,3-Dibromo-5,5-dimethylhydantoin (DBH), as a cheap and commercially available reagent, is efficiently able to catalyze the synthesis of polyhydroquinoline derivatives and 12-aryl-8,9,10,12-tetrahydro[a] xanthene-11-ones via one-pot multi-component reactions. This novel synthetic method has the advantages of low cost and availability of the catalyst, short reaction times, high to excellent yiel...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:
  • Tetrahedron letters

دوره 53 26  شماره 

صفحات  -

تاریخ انتشار 2012