A general and convenient synthesis of 4-(tosylmethyl)semicarbazones and their use in amidoalkylation of hydrogen, heteroatom, and carbon nucleophiles. Issue 45 (8th November 2019)

• Record Type: Journal Article
• Authors: Fesenko, Anastasia A.; Yankov, Alexander N.; Shutalev, Anatoly D.
• Is Part Of: Tetrahedron. Volume 75:Issue 45(2019)
• Publication Date: 2019-11-08
• Subjects: Semicarbazones -- Three-component condensation -- Sulfones -- Amidoalkylation -- Nucleophiles -- Antibacterial and antifungal activity; XLAANFZTRILRNR-MHWRWJLKSA-N -- DNDFEGLKDMCPKS-GXDHUFHOSA-N -- LLVCNTONYRPRMI-WOJGMQOQSA-N -- FEZJZCWQZWEJPO-DEDYPNTBSA-N -- RZLVGGROKOHKBT-XQNSMLJCSA-N -- VQEWHOVGSBVRSG-XSFVSMFZSA-N -- BQGYZFUPWCZMPF-IZZDOVSWSA-N -- OVNFYWRWAVXONE-KGENOOAVSA-N -- JRLOZSBXPXLLSE-DEDYPNTBSA-N -- YSBUOHYZTZIYFW-XDHOZWIPSA-N -- RKKCBTABQWQPQN-HZHRSRAPSA-N -- KAGYZAPDQSMTMU-WOJGMQOQSA-N -- WQBLSMNXXLUMKM-XNTDXEJSSA-N -- XMOSPRNBIZDFKS-MFKUBSTISA-N -- RBBNBTUQATZIMZ-PXLXIMEGSA-N -- SCGMBUMWQVKGPR-QGOAFFKASA-N -- NWSVUUFRILBFGP-XNTDXEJSSA-N -- LPCLVQKZJCREJI-YBFXNURJSA-N -- MKRCBXZKYZLFKB-OVVQPSECSA-N -- XWYFBVDNNVRTON-OEAKJJBVSA-N -- OPZPQMNPUJCKJW-UKTHLTGXSA-N -- STJTXAUKYNJTMI-LICLKQGHSA-N -- OUGFTWAMMNKOBR-XSFVSMFZSA-N -- XNDDSWOHTOWLEG-LFVJCYFKSA-N -- ARXAIZGVUZXIMT-AWNIVKPZSA-N -- YRINZPDCPRYNPP-PXLXIMEGSA-N -- QVIREZBYIATAKY-XDHOZWIPSA-N -- MEEMACNEJZZBFC-HYARGMPZSA-N -- KVWYUXNEHCATNO-VXLYETTFSA-N -- OCGRLKFAJHCHDH-LPYMAVHISA-N -- BXPMRMHHAYESBJ-MFKUBSTISA-N -- JPBCPCFREZWRCA-PCLIKHOPSA-N -- WPMGJWANJDOKMO-NTEUORMPSA-N -- XBIAZGANKLDHKH-PCLIKHOPSA-N -- ZTZWXHAZHOVMPU-FYJGNVAPSA-N -- DSKZKXAVXLKTCB-PCLIKHOPSA-N -- QPHNLROCLCRLCD-WUXMJOGZSA-N -- AQODKBWUYMMBCC-LFIBNONCSA-N -- RFKHKOJCBVHMQY-XNTDXEJSSA-N -- IIMJOIYPWQEZMT-SFQUDFHCSA-N -- DULWFZHKDAQRGR-LFVJCYFKSA-N -- CDBMNFHBHZDNMW-LICLKQGHSA-N -- JWSOORCSTAZLCF-CPNJWEJPSA-N -- VMCDTABRFWPWOX-LFVJCYFKSA-N -- LEGLCWMQCYZZJT-LDADJPATSA-N -- KYJVXPVURBIZSC-DEDYPNTBSA-N -- RQEODZVERCNWCT-KPKJPENVSA-N -- YCVVNIZNKINTAQ-PXLXIMEGSA-N -- FCQDLDGBGNZHLA-LPYMAVHISA-N -- XBSJUPHGIPBNIE-AJBULDERSA-N -- OYADNMHMQCVBNG-HZHRSRAPSA-N -- MLAQSTZAQNFRGC-GZTJUZNOSA-N -- GBZYUNMPSBEORO-XDHOZWIPSA-N -- JTYBIHPRYWKREX-VCHYOVAHSA-N -- WTLORHGFWYRAKL-KGENOOAVSA-N -- FYBRSXQFLQCKEK-PCLIKHOPSA-N -- SWLQWLCGXVEFJY-WOJGMQOQSA-N -- PZOANRXICRSIRH-KPKJPENVSA-N -- MRLVYYCVRDWENG-XNTDXEJSSA-N -- ZTFHZSDLOJKNKU-LFIBNONCSA-N -- XABMEBLITPWLNB-XDHOZWIPSA-N -- RMMLXXWKDPUWDF-HZHRSRAPSA-N -- XYXUAXXHFGBJTA-LZYBPNLTSA-N -- NKSYRWOFCVPIJW-SFQUDFHCSA-N -- JWSPFJOSHDPZTD-PXLXIMEGSA-N -- KBUBNURUNVPACW-GZTJUZNOSA-N -- KNGKYITWFKOXFT-OQLLNIDSSA-N -- IJXLQQAODHPIMM-HMMYKYKNSA-N -- QONPYBDFQKZOQR-PCLIKHOPSA-N -- DGMZBGQHLABHPM-KGENOOAVSA-N -- OAQJICUXDGKCNR-RDRPBHBLSA-N; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2019.130527
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A general synthesis of previously unknown semicarbazone-based α-amidoalkylating reagents, 4-(tosylmethyl)semicarbazones, has been developed. The synthesis involved three-component condensation of semicarbazones of aliphatic or aromatic aldehydes with the same or other aldehydes and p -toluenesulfinic acid. The scope and limitations of this reaction were investigated. The compounds obtained were demonstrated to be an efficient α-(4-semicarbazono)alkylating agents. They were reacted with H - (sodium borohydride), O - (sodium methylate), S - (sodium phenylthiolate), N - (pyrrolidine, sodium succinimide), P - (trialkyl phosphites), and C -nucleophiles (sodium diethyl malonate) to give the corresponding products of the tosyl group substitution, 4-substituted semicarbazones, including analogues of nitrofurazone. Among the prepared compounds tested in vitro for antibacterial and antifungal activity, three nitrofuryl-containing semicarbazones exhibited high biological activities with minimum inhibitory concentration (MIC) values of 8–32 μg/mL. Graphical abstract: Image 1 Highlights: Novel amidoalkylating reagents based on semicarbazones were prepared. Amidoalkylation of some H -, O -, S -, N -, P -, and C -nucleophiles was studied. 4-Substituted semicarbazones, in particular, α-functionalized ones, were obtained. Some prepared compounds possess antibacterial and antifungal activities.