ChemInform Abstract: ortho-Directed Lithiation Studies of 4-Chloropicolinanilide: Introduction of Functional Groups at C-3 and Their Elaboration to Chain Extended Derivatives via Carbon—Carbon Bond Formation.
✍ Scribed by M. V. N. DE SOUZA; R. H. DODD
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 37 KB
- Volume
- 29
- Category
- Article
- ISSN
- 0931-7597
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✦ Synopsis
ortho-Directed Lithiation Studies of 4-Chloropicolinanilide: Introduction of Functional Groups at C-3 and Their Elaboration to Chain Extended Derivatives via Carbon-Carbon Bond Formation.
-4-Chloropicolinamide (III), prepared by an optimized procedure from picolinic acid (I), undergoes selective LDA lithiation and subsequent reaction with various electrophiles at the 3-position. The methyl derivative (VII) can be elaborated to chain-extended derivatives. Heck-type reaction of the 3-iodo compound (X) with the acrylic compounds (XI) gives directly the cyclized products. Finally, radical cyclization of the allylic ether (XIV) provides a furopyridine. -(DE