Cu0-catalysed 1, 3-dipolar cycloadditions of α-amino acid derived N, N-cyclic azomethine imines to ynones. Issue 24 (15th June 2017)

• Record Type: Journal Article
• Authors: Mirnik, Jona; Pušavec Kirar, Eva; Ričko, Sebastijan; Grošelj, Uroš; Golobič, Amalija; Požgan, Franc; Štefane, Bogdan; Svete, Jurij
• Is Part Of: Tetrahedron. Volume 73:Issue 24(2017)
• Page Start: 3329
• Page End: 3337
• Publication Date: 2017-06-15
• Subjects: Azomethine imines -- Ynones -- Copper -- Catalysis -- 1, 3-Dipolar cycloadditions; AYYHAMKZLZBTPF-BWDPKJPESA-N -- RDUQICUQTSNERX-VSKRKVRLSA-N -- BGDCIXPCLRPFSB-PFBJBMPXSA-N -- QKSLPCQYRUNLJA-UODIDJSMSA-N -- RDJVHZWZHLXQFP-JPSPSYKNSA-N -- VLBNKMJYALYHRR-TZRRMPRUSA-N -- QXLKUFJSELORMF-SDHSZQHLSA-N -- QWESOFZULXXVIN-ICODJCHTSA-N -- RAEYGCRLPDVKRL-VSKRKVRLSA-N -- VCHYLZCLAHDTEF-PFBJBMPXSA-N -- SAIHUIAUDGZHMR-VXGBXAGGSA-N -- AHCYPXCOIFPBMD-GMAHTHKFSA-N -- RPGMDXLPJVOWAW-OGHMMLIOSA-N -- NVINBZSMUOAWBD-UODIDJSMSA-N -- FXQDOZPYGNCNLB-MJSOWUPRSA-N -- MFEIWKNGIWRDSI-ZLNRFVROSA-N -- CZNRYRFUXFMGLN-BDQMVGTNSA-N -- JYOJAOQAJOXWQE-KWXIBIRDSA-N -- RYKSQFXSOWFUDJ-JTQLQIEISA-N -- RRIYMZSWHUUBCG-PJIZFRNJSA-N -- QXNLBQSDPIEGJE-CTBXZWMSSA-N -- ZCIAGWIURXWYSK-SMIHKQSGSA-N -- RINFDUOJBCCIFX-NLDZOOGBSA-N -- JOICTNRUICKYKF-ZIAGYGMSSA-N -- NCXNPGOMTHZHSK-FCEKVYKBSA-N -- PKIXJMBQZVJDMH-LEMNDLQOSA-N -- BZRFBMQGHOKWER-DSNGMDLFSA-N -- JOGWBBRVNSGKIU-ZLNRFVROSA-N -- PQHIZXBPKSWLFV-PMACEKPBSA-N -- NHDAYTFQXITMLA-YCCHBACSSA-N -- IIHCGXFHVWAGJA-PMACEKPBSA-N -- MPARCZWCPQRFDX-SMIHKQSGSA-N -- QHBPDVDTWKULTK-VIFPVBQESA-N -- CFBFYDGUIJTIGZ-AOUKMLRZSA-N; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2017.04.050
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A series of 20 CuAIAC reactions between eight 4-acylamino substituted pyrazolidine-3-one-1-azomethine imines and four terminal ynones were performed using Cu 0 as catalyst. The corresponding fluorescent cycloadducts were obtained in very high yields upon simple workup. Thus, Cu-metal turned out to be a better catalyst than Cu I in terms of yield and ease of isolation. Availability of azomethine imines, mild reaction conditions, and simple workup enable a "click" access to libraries of densely substituted 2, 3-dihydro-1 H, 5 H -pyrazolo[1, 2- a ]pyrazol-1-ones. Reactivity of differently substituted dipoles was evaluated experimentally and by quantum chemical methods (DFT). Graphical abstract: