| Publication Type |
Journal Article |
| Title |
Phosphane-Catalyzed [3+2] Annulation of Allenoates with 3-Nitro-2H-chromenes: Synthesis of Tetrahydrocyclopenta[c]chromenes |
| Authors |
Maria I. L. Soares Clara S. B. Gomes Sandra C. C. Nunes Alberto A. C. C. Pais Teresa M. V. D. Pinho e Melo |
| Groups |
IOARC |
| Journal |
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY |
| Year |
2019 |
| Month |
September |
| Volume |
2019 |
| Number |
31 |
| Pages |
5441-5451 |
| Abstract |
The synthesis of carbocyclic-fused chromene derivatives based on allene chemistry is described. The phosphane-catalyzed [3+2] annulation reactions of allenic esters with 3-nitrochromenes have been established affording 3a-nitro-tetrahydrocyclopenta[c]chromenes in good yields (up to 87 \%) with high stereo- and regioselectivity. Quantum chemical calculations, carried out at the DFT level of theory, were in agreement with the observed selectivity. The trichlorosilane-mediated reduction of the 3a-nitro-tetrahydrocyclopenta[c]chromenes into the corresponding amines is also reported. |
| DOI |
http://dx.doi.org/10.1002/ejoc.201900564 |
| ISBN |
|
| Publisher |
|
| Book Title |
|
| ISSN |
1434-193X |
| EISSN |
1099-0690 |
| Conference Name |
|
| Bibtex ID |
ISI:000483709700048 |
| Observations |
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