A simple, tandem approach to the construction of pyridine derivatives under metal-free conditions: a one-step synthesis of the monoterpene natural product, (−)-actinidine
| Autor: | E. Blake Watkins, Dilipkumar Uredi, Damoder Reddy Motati |
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| Rok vydání: | 2019 |
| Předmět: |
Natural product
Iridoid Tandem 010405 organic chemistry medicine.drug_class Monoterpene Imine Metals and Alloys Substrate (chemistry) General Chemistry 010402 general chemistry 01 natural sciences Combinatorial chemistry Catalysis 0104 chemical sciences Surfaces Coatings and Films Electronic Optical and Magnetic Materials Actinidine chemistry.chemical_compound chemistry Pyridine Materials Chemistry Ceramics and Composites medicine |
| Zdroj: | Chemical Communications. 55:3270-3273 |
| ISSN: | 1364-548X 1359-7345 |
| DOI: | 10.1039/c9cc01097a |
| Popis: | A simple and modular one-step synthesis of diversely substituted pyridines from readily available α,β-unsaturated carbonyl compounds and propargylic amines has been developed. The present protocol has a broad substrate scope and allows access to multi-substituted pyridines with select control of the substitution pattern under mild and metal-free conditions. The reaction involves imine formation followed by concomitant cyclization through an allenyl intermediate to afford pyridines in excellent yields, with water as the sole by-product. This mild strategy is also suitable for functionalization of natural products or other advanced intermediates having α,β-unsaturated carbonyl functionality. The utility of the present protocol was showcased with the synthesis of the monoterpene alkaloid, (-)-actinidine, an ant-associated iridoid. |
| Databáze: | OpenAIRE |
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