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Convenient Synthesis of Pyrazolo[4′,3′:5,6]pyrano[4,3-c][1,2]oxazoles via Intramolecular Nitrile Oxide Cycloaddition
| Content Provider | MDPI |
|---|---|
| Author | Vaida, Milišiūnaitė Elena, Plytninkienė Roberta, Bakšienė Sonata, Krikštolaitytė Greta, Račkauskienė Egl, ė Arbačiauskienė Algirdas, Šačkus Bieliauskas, Aurimas |
| Copyright Year | 2021 |
| Description | A simple and efficient synthetic route to the novel 3a,4-dihydro-3H,7H- and 4H,7H-pyrazolo[4′,3′:5,6]pyrano[4,3-c][1,2]oxazole ring systems from 3-(prop-2-en-1-yloxy)- or 3-(prop-2-yn-1-yloxy)-1H-pyrazole-4-carbaldehyde oximes has been developed by employing the intramolecular nitrile oxide cycloaddition (INOC) reaction as the key step. The configuration of intermediate aldoximes was unambiguously determined using NOESY experimental data and comparison of the magnitudes of$ $^{1}$J_{CH}$ coupling constants of the iminyl moiety, which were greater by approximately 13 Hz for the predominant syn isomer. The structures of the obtained heterocyclic products were confirmed by detailed$ ^{1}$H,$ ^{13}$C and$ ^{15}$N NMR spectroscopic experiments and HRMS measurements. |
| Starting Page | 5604 |
| e-ISSN | 14203049 |
| DOI | 10.3390/molecules26185604 |
| Journal | Molecules |
| Issue Number | 18 |
| Volume Number | 26 |
| Language | English |
| Publisher | MDPI |
| Publisher Date | 2021-09-15 |
| Access Restriction | Open |
| Subject Keyword | Molecules Pyrazole Isoxazoline/isoxazole Fused Ring Systems Intramolecular Nitrile Oxide Cycloaddition 4-pyrazolaldoximes 1jch Isoxazole 15n Nmr Isoxazoline 15n Nmr |
| Content Type | Text |
| Resource Type | Article |
