Synthesis, Inhaltsverzeichnis Synthesis 2019; 51(15): 2891-2896DOI: 10.1055/s-0037-1611836 psp © Georg Thieme Verlag Stuttgart · New York Synthesis of N-Pyridyl Hydroxylamines via Copper-Catalyzed Cross-Coupling Carilyn Torruellas* CCDC Chemical Biological Center, 8198 Blackhawk Rd., Aberdeen Proving Ground, MD 21010, United States eMail: carilyn.torruellaspagan.civ@mail.mil , Fu-Lian Hsu , Andrew J. Walz › Institutsangaben Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract N-Pyridyl hydroxylamine derivatives were prepared via copper-catalyzed cross-coupling of orthogonally functionalized hydroxylamines with iodopyridines. Various amino- and hydroxyl-protecting groups were tolerated. A total of 20 examples were synthesized in 28–90% yield. Key words Key wordscopper - cross-coupling - hydroxylamines - protecting groups - pyridine Volltext Referenzen References 1a Wencewicz TA, Yang B, Rudloff JR, Oliver AG, Miller MJ. J. Med. Chem. 2011; 54: 6843 1b Krchnak V, Zajicak J, Miller P. J. Org. Chem. 2011; 75: 10249 2a Culyba M, Hwang Y, Attar S, Madrid PB, Bupp J, Huryn D, Sanchez L, Grobler J, Miller MD, Bushman FD. Nucleic Acids Res. 2012; 40: 1 2b Zhao ZX, Smith SJ, Metifiot M, Johnson BC, Marchand C, Pommier Y, Hugher SH, Burke TR. J. Med. Chem. 2014; 57: 1573 2c Zhao ZX, Smith SJ, Metifiot M, Marchand C, Boyer PL, Pommier Y, Hugher SH, Burke TR. J. Med. Chem. 2014; 57: 5190 2d Zhao ZX, Smith SJ, Maskell DP, Metifiot M, Pye VE, Fesen K, Marchand C, Pommier Y, Hugher SH, Burke TR. J. Med. Chem. 2017; 60: 7315 2e Zhao ZX, Smith SJ, Maskell DP, Metifiot M, Pye VE, Fesen K, Marchand C, Pommier Y, Cherepanov P, Hugher SH, Burke TR. ACS Chem. Biol. 2016; 11: 1074 3 Tseng CH, Lin RW, Chen YL, Wang GJ, Ho ML, Tzeng CC. J. Med. Chem. 2011; 54: 3103 4 Disadee W, Ploypradith P, Aree T, Chaichit N, Ruchirawat S. Tetrahedron Lett. 2011; 52: 6142 5 Hand ES, Paudler WW. J. Heterocycl. Chem. 1975; 12: 1063 6 Kuzmich D, Mulrooney C. Synthesis 2003; 1671 7a Tomazic A, Tisler M, Stanovik B. Tetrahedron 1981; 37: 1787 7b Demeunynck M, Tohme N, Lhomme MF, Lhomme J. J. Heterocycl. Chem. 1984; 21: 501 Examples of nitroso ene and nitroso aldol reactions: 8a Yang B, Miller M. Tetrahedron Lett. 2010; 51: 328 8b Li Y, Chakrabarty S, Armido S. Angew. Chem. Int. Ed. 2015; 54: 3587 Turbo Grignard reactions: 9a Bogart JA, Lee HB, Boreen MA, Jun M, Schelter EJ. J. Org. Chem. 2013; 78: 6344 9b Okazawa A, Nogami T, Ishida T. Chem. Mater. 2007; 19: 2733 10 Nitroso Diels–Alder reaction: Krchnak V, Moellmann U, Dahse HM, Miller MJ. J. Comb. Chem. 2008; 10: 104 11a Hartwig JF. Acc. Chem Res. 2008; 41: 1534 11b Muci AR, Buchwald SL. Cross-Coupling Reactions: A Practical Guide . In Topics in Current Chemistry, Vol. 219. Miyaura N. Springer; Berlin: 2002: 131 11c Wagaw S, Buchwald S. J. Org. Chem. 1996; 61: 7240 12 Kukosha T, Trufilkina N, Belyakov S, Katkevics M. Synthesis 2012; 44: 2413 13 Jones KL, Porzelle A, Hall A, Woodrow MD, Tomkinson NC. O. Org. Lett. 2008; 10: 797 Zusatzmaterial Zusatzmaterial Supporting Information
