3-Cyanoallyl boronates are versatile building blocks in the synthesis of polysubstituted thiophenes† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c7sc00831g Click here for additional data file.

نویسندگان

  • Wenjie Shao
  • Sherif J. Kaldas
  • Andrei K. Yudin
چکیده

We report the preparation of hitherto unprecedented 3-cyanoallyl boronates using condensation of the parent a-boryl aldehyde and nitriles. The resulting allyl boronates have been used to generate a wide range of borylated thiophenes, which represent a valuable class of heterocycles in modern drug discovery. Subsequent Suzuki–Miyaura cross-coupling enabled the synthesis of pharmaceutically important 3,5-disubstituted aminothiophenes. Moreover, late stage functionalization gave access to borylated bromothiophene and thieno[2,3-b]pyridines.

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منابع مشابه

(Phosphanyl)phosphaketenes as building blocks for novel phosphorus heterocycles† †Electronic supplementary information (ESI) available: Characterization data, crystallographic data and Cartesian coordinates of DFT optimized structures. CCDC 1432815(4), 1432814 (5), 1528506 (6), 1432817 (8), 1528508 (10) and 1528507 (10′). For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7sc00300e Click here for additional data file. Click here for additional data file.

1. General Information ............................................................................................................................. 1 2. Synthesis and Characterization data ................................................................................................... 2 3. X-ray data ..............................................................................................

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Ru-catalyzed sequence for the synthesis of cyclic amido-ethers† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c6sc02849g Click here for additional data file.

Efficient synthesis of versatile building blocks for enabling medicinal chemistry research has always challenged synthetic chemists to develop innovative methods. Of particular interest are the methods that are amenable to the synthesis of chemically distinct and diverse classes of pharmaceutically relevant motifs. Herein we report a general method for the one-pot synthesis of cyclic α-amido-et...

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عنوان ژورنال:

دوره 8  شماره 

صفحات  -

تاریخ انتشار 2017