Silver-Catalyzed Tandem Synthesis of Naphthyridines and Thienopyridines via Three-Component Reaction
| Autor: | Rakesh Tiwari, Akhilesh K. Verma, Deepak Choudhary, Monika Patel, Siva K. Reddy Kotla |
|---|---|
| Rok vydání: | 2013 |
| Předmět: |
Magnetic Resonance Spectroscopy
Silver Molecular Structure Thienopyridines Tandem Chemistry Organic Chemistry Regioselectivity chemistry.chemical_element Chemistry Techniques Synthetic Combinatorial chemistry Sulfur Catalysis chemistry.chemical_compound Electrophile Organic chemistry Reactivity (chemistry) Naphthyridines Methylene |
| Zdroj: | The Journal of Organic Chemistry. 78:4386-4401 |
| ISSN: | 1520-6904 0022-3263 |
| Popis: | An efficient approach for the silver-catalyzed regioselective tandem synthesis of highly functionalized 1,2-dihydrobenzo[1,6]naphthyridines 6a-z and 7a-e by the reaction of ortho-alkynylaldehydes 3a-n with amines 4a-d and ketones 5a-c/active methylene compounds 5d-g, under mild reaction conditions, is described. The scope of the developed chemistry was successfully extended for the direct synthesis of 1,2-dihydrobenzo[4,5]thieno[2,3-c]pyridines 8a-e, which is known as the sulfur analogue of β-carbolines. Naphthyridines 6a-z and thienopyridines 8a-e were obtained via dual activation concept using l-proline as organocatalyst; however, naphthyridines 7a-e were synthesized without using organocatalyst. The reaction shows selective N-C bond formation on the more electrophilic alkynyl carbon, resulting in the regioselective 6-endo-dig-cyclized products. Reactivity behavior of electron-deficient and electron-rich ortho-alkynylaldehydes in the synthesis of naphthyridines and thienopyridine by three-component reaction is supported by the control experiment. |
| Databáze: | OpenAIRE |
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