A highly efficient [3+2] cycloaddition of nitrile oxides and azomethine imines to N-vinylpyrroles. Issue 14 (8th April 2015)

• Record Type: Journal Article
• Authors: Efremova, Mariia M.; Molchanov, Alexander P.; Stepakov, Alexander V.; Kostikov, Rafael R.; Shcherbakova, Victoriya S.; Ivanov, Andrey V.
• Is Part Of: Tetrahedron. Volume 71:Issue 14(2015)
• Page Start: 2071
• Page End: 2078
• Publication Date: 2015-04-08
• Subjects: Pyrroles -- Cycloaddition -- Nitrile oxides -- Azomethine imines -- Stereoselectivity; BCTSRQVVAYOWHF-UHFFFAOYSA-N -- WQLAPEVMVZCCCG-PMACEKPBSA-N -- ZLXUUUCATIFWBN-UHFFFAOYSA-N -- FZWZIFSMDYWUFE-RTWAWAEBSA-N -- AQOMEBVKKXUSNB-HKUYNNGSSA-N -- RFMCZVQEXMNLJR-UHFFFAOYSA-N -- FKVOAMRMBQRDQV-UHFFFAOYSA-N -- BEGSFWTXDCVVJL-OALUTQOASA-N -- RRLJRCOJRYFCHS-YADHBBJMSA-N -- YEQVQDSEJSBNDZ-UHFFFAOYSA-N -- UPCUCURXVAWDIV-RTWAWAEBSA-N -- SSFYJYLSYCWQMW-RTWAWAEBSA-N -- IDGSNQCMMWFLLY-OALUTQOASA-N -- GLOLOBJLRCHZMX-UHFFFAOYSA-N -- QMVGWBOMHMONMR-YADHBBJMSA-N -- QMVGWBOMHMONMR-VXKWHMMOSA-N -- CNKWEIRXCSJYGZ-UHFFFAOYSA-N -- IHPCMTNKKBUOLJ-CTNGQTDRSA-N -- BEGSFWTXDCVVJL-MOPGFXCFSA-N -- AQOMEBVKKXUSNB-MJGOQNOKSA-N -- IJCOLUSIEMZOIK-UHFFFAOYSA-N -- FZWZIFSMDYWUFE-SFTDATJTSA-N -- RVWIDNMUYFWWPB-UXHICEINSA-N -- BYNSLGHYCNWDTR-UHFFFAOYSA-N -- WXFIZQNIOVJUFD-QUCCMNQESA-N -- WXFIZQNIOVJUFD-ICSRJNTNSA-N -- OOGAGXQMTJEDQP-UHFFFAOYSA-N -- IDGSNQCMMWFLLY-MOPGFXCFSA-N -- RVWIDNMUYFWWPB-PMACEKPBSA-N -- UPCUCURXVAWDIV-SFTDATJTSA-N -- SRVCCUQVWZVPNK-UHFFFAOYSA-N -- FBLQQULQUBQQBA-PKTZIBPZSA-N -- WQLAPEVMVZCCCG-UXHICEINSA-N; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2015.02.058
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: 1, 3-Dipolar cycloaddition of various nitrile oxides to substituted N -vinylpyrroles proceed with high efficiency and selectivity with the formation of single isomer of 5-pyrrolyl-substituted isoxazoline. The reaction of N -vinylpyrroles with cyclic azomethine imines occurs regioselectively affording 7-(pyrrol-1-yl)- substituted pyrazolo[1, 2- a ]pyrazolones as a mixture of two diastereomers. Graphical abstract: