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http://hdl.handle.net/11701/1960
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Поле DC | Значение | Язык |
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dc.contributor.author | Novikov, Mikhail S. | - |
dc.contributor.author | Khlebnikov, Alexander F. | - |
dc.contributor.author | Rostovskii, Nikolai V. | - |
dc.contributor.author | Tcyrulnikov, Sergei | - |
dc.contributor.author | Suhanova, Anna A. | - |
dc.contributor.author | Zavyalov, Kirill V. | - |
dc.contributor.author | Yufit, Dmitry S. | - |
dc.date.accessioned | 2016-04-07T21:14:47Z | - |
dc.date.available | 2016-04-07T21:14:47Z | - |
dc.date.issued | 2015-01 | - |
dc.identifier.citation | J. Org. Chem. 2015, 80, 18−29 | en_GB |
dc.identifier.issn | 0022-3263 | - |
dc.identifier.uri | http://hdl.handle.net/11701/1960 | - |
dc.description.abstract | Transformations of 2-azabuta-1,3-dienes, formed in Rh2(OAc)4-catalyzed reactions of diazo carbonyl compounds with 2H-azirines, dramatically depend on the nature of substituents. 4,4-Diphenyl-2-azabuta-1,3-dienes with two electron-acceptor substituents at C1 undergo thermal 1,5-cyclization to give indoles in good yields. The increase in electronwithdrawing ability of C1-substituents facilitates the reaction that proceeds via pseudopericyclic 1,5-electrocyclization of 2-azabutadiene into 7aH-indolium ylide followed by prototropic shift. 3,4-Diphenyl-2-azabuta-1,3-dienes, resulting from reaction of 2,3-diphenyl-2H-azirine and diazo compounds, do not produce indoles via 1,5-cyclization due to the trans-configuration of the 4-Ph-group and the nitrogen, but undergo 1,4-cyclization to 2,3-dihydroazetes. 1,6-Cyclization into 2H-1,4-oxazines with participation of the oxygen of ester or amide group at C1 of corresponding 2-azabuta-1,3-dienes does not take place due to kinetic and thermodynamic reasons. Instead of this, 1,6-electrocyclization with participation of phenyl substituent at C4 of the 2-azabuta-1,3-dienes, providing isoquinoline derivatives, can occur at elevated temperatures. The DFT-calculations (mPWB1K/6-31+G(d,p)) confirm the dependence of 2-azabuta-1,3-diene transformation type on the nature of substituents. | en_GB |
dc.language.iso | en | en_GB |
dc.publisher | American Chemical Society | en_GB |
dc.relation.ispartofseries | The Journal of Organic Chemistry;Vol. 80 | - |
dc.subject | 2-azabuta-1,3-dienes | en_GB |
dc.subject | Indole Synthesis | en_GB |
dc.subject | Azirines | en_GB |
dc.subject | Diazo Compounds | en_GB |
dc.subject | Pseudopericyclic reactions | en_GB |
dc.subject | Pericyclic reactions | en_GB |
dc.title | Pseudopericyclic 1,5- versus Pericyclic 1,4- and 1,6-Electrocyclization in Electron-Poor 4‑Aryl-2-azabuta-1,3-dienes: Indole Synthesis from 2H‑Azirines and Diazo Compounds | en_GB |
dc.type | Article | en_GB |
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