Directed Ortho Metalation−Cross Coupling Strategies. N -Cumyl Arylsulfonamides. Facile Deprotection and Expedient Route to 7- and 4,7-Substituted Saccharins
| Autor: | Jérôme Blanchet, Victor Snieckus, Todd Macklin, Patrick Ang, Costa Metallinos |
|---|---|
| Přispěvatelé: | Queen's University [Kingston, Canada] |
| Jazyk: | angličtina |
| Rok vydání: | 2007 |
| Předmět: |
Metalation
Stereochemistry medicine.drug_class Chemistry Organic Thiazines Carboxamide 010402 general chemistry 01 natural sciences Chemical synthesis Aldehyde Medicinal chemistry chemistry.chemical_compound Saccharin Suzuki reaction Amide medicine ComputingMilieux_MISCELLANEOUS chemistry.chemical_classification Sulfonamides 010405 organic chemistry [CHIM.ORGA]Chemical Sciences/Organic chemistry Organic Chemistry 0104 chemical sciences Sulfonamide chemistry Metals Directed ortho metalation |
| Zdroj: | Journal of Organic Chemistry Journal of Organic Chemistry, American Chemical Society, 2007, 72 (9), pp.3199-3206. ⟨10.1021/jo062385v⟩ |
| ISSN: | 0022-3263 1520-6904 |
| DOI: | 10.1021/jo062385v⟩ |
| Popis: | By using the powerful N-cumylsulfonamide directed metalation group (DMG), a series of 2-substituted derivatives were prepared according to the directed ortho metalation (DoM) tactic (Table 1). Mild conditions for N-decumylation and other simple transformations of the products have been achieved (Scheme 2). The 3-silyloxy sultam 12 undergoes further DoM to give formyl, thiomethyl, iodo, and amide derivatives 13a−g of potential value for saccharin synthesis (Table 2). An effective route to target 7-aryl saccharins via Suzuki cross coupling (Table 3) followed by further metalation−carbamoylation and cyclization (Table 5) is described. 4,7-Disubstituted saccharins have been obtained by similar sequences (Scheme 3). Mild TFA-mediated N-decumylation furnishes substituted primary arylsulfonamides (Table 4). |
| Databáze: | OpenAIRE |
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