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Facile, Diversity-Oriented, Normal-Electron-Demand Diels–Alder Reactions of 6-Amino-2H-pyran-2-ones with Diethyl Acetylenedicarboxylate, 1,4-Naphthoquinone, and N-Phenylmaleimide
| Content Provider | Scilit |
|---|---|
| Author | Samant, Shriniwas D. Khatri, Adil I. |
| Copyright Year | 2014 |
| Description | A series of 6-amino-4-methoxyphenyl-2H-pyran-2-ones, having an electron-rich diene system, capable of undergoing normal-electron-demand (NED) Diels–Alder reaction, were synthesized. The Diels–Alder reaction of these pyrones with electron-deficient dienophiles – diethyl acetylene dicarboxylate, 1,4-naphthoquinone, and N-phenylmaleimide – followed three different pathways and gave structurally diverse products, aminobenzenes, aminoanthraquinones, and aminopolycyclic diimides, respectively. The amino group at the 6-position activated substantially the pyrone ring towards NED Diels–Alder reaction and the reaction has a potential to generate great structural diversity. |
| Related Links | http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0034-1379397.pdf |
| Ending Page | 350 |
| Page Count | 8 |
| Starting Page | 343 |
| ISSN | 00397881 |
| e-ISSN | 1437210X |
| DOI | 10.1055/s-0034-1379397 |
| Journal | Synthesis |
| Issue Number | 03 |
| Volume Number | 47 |
| Language | English |
| Publisher | Georg Thieme Verlag KG |
| Publisher Date | 2014-11-13 |
| Access Restriction | Open |
| Subject Keyword | Journal: Synthesis Organic Chemistry 6-amino-2h-pyrone Normal-electron-demand Diels–alder Reaction Diversity-oriented Synthesis Polycyclic Diimides |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Catalysis |