Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Download PDF
Synthesis 2007(19): 3083-3087
DOI: 10.1055/s-2007-983828
DOI: 10.1055/s-2007-983828
PSP
© Georg Thieme Verlag Stuttgart · New YorkPalladium-Catalyzed Oxidative Aminocarbonylation of Alkynols
Further Information
Received
2 March 2007
Publication Date:
30 July 2007 (online)
Publication History
Publication Date:
30 July 2007 (online)
Abstract
Alkynols undergo palladium-catalyzed aminocarbonylation leading to the direct formation of different heterocyclic derivatives, depending on the position of the OH group with respect to the triple bond. In the cases of 4-yn-1-ols and (Z)-2-en-4-yn-1-ols, the initially formed 2-ynamide intermediates, respectively, undergo cyclization leading to tetrahydrofuran derivatives or 2-furan-2-ylacetamides, respectively. In the case of 2-yn-1-ols, the aminocarbonylation products undergo intermolecular conjugate addition, followed by lactonization, leading to aminofuranones.
Key words
aminocarbonylation - carbonylations - cyclization - heterocycles - palladium
- 1a
Gabriele B.Salerno G.Costa M. Top. Organomet. Chem. 2006, 18: 239MissingFormLabel - 1b
Muzart J. Tetrahedron 2005, 61: 9423MissingFormLabel - 1c
Vizer SA.Yerzhanov KB.Al Quntar AAA.Dembitsky VM. Tetrahedron 2004, 60: 5499MissingFormLabel - 1d
Alonso F.Beletskaya IP.Yus M. Chem. Rev. 2004, 104: 3079MissingFormLabel - 1e
Zeni G.Larock RC. Chem. Rev. 2004, 104: 2285MissingFormLabel - 1f
Nakamura I.Yamamoto Y. Chem. Rev. 2004, 104: 2127MissingFormLabel - 1g
Gabriele B.Salerno G. In Handbook of Organopalladium Chemistry for Organic Synthesis Vol. 2:Negishi E. Wiley-Interscience; New York: 2002. p.2623MissingFormLabel - 2a
Gabriele B.Salerno G.Costa M.Chiusoli GP. Curr. Org. Chem. 2004, 8: 919 - 2b
Gabriele B.Salerno G.Costa M. Synlett 2004, 2468 - 2c
Gabriele B.Salerno G.Costa M.Chiusoli GP. J. Organomet. Chem. 2003, 687: 219 - For other very important examples, see:
- 2d
Gabriele B.Salerno G.Fazio A.Veltri L. Adv. Synth. Catal. 2006, 348: 2212 - 2e
Gabriele B.Salerno G.Veltri L.Mancuso R.Li Z.Crispini A.Bellusci A. J. Org. Chem. 2006, 71: 7895 - 2f
Bacchi A.Costa M.Della CN.Gabriele B.Salerno G.Cassoni S. J. Org. Chem. 2005, 70: 4971 - 2g
Gabriele B.Salerno G.Plastina P.Costa M. Synlett 2005, 935 - 3
Gabriele B.Salerno G.Veltri L.Costa M. J. Organomet. Chem. 2001, 622: 84 - 4
Gabriele B.Salerno G.Plastina P. Lett. Org. Chem. 2004, 1: 134 - 5
Gabriele B.Plastina P.Salerno G.Mancuso R. Synthesis 2006, 4247 - 6
Baldwin JE. J. Chem. Soc., Chem. Commun. 1976, 734 - 7
Gabriele B.Salerno G.Plastina P.Costa M.Crispini A. Adv. Synth. Catal. 2004, 346: 351 - 8
Gabriele B.Salerno G.Mancuso R.Costa M. J. Org. Chem. 2004, 69: 4741 - 9a
Shen M.Beguin C.Golbraikh A.Stables JP.Kohn H.Tropsha A. J. Med. Chem. 2004, 47: 2356 - 9b
Prasad CVC.Shikha V.Smith DW.Gao Q.Polson CT.Corsa JA.Guss VL.Loo A.Barten DM.Zheng M.Felsenstein KM.Roberts SB. Bioorg. Med. Chem. Lett. 2004, 14: 3535 - 9c
Sheehan SM.Masters JJ.Wiley MR.Young SC.Liebeschuetz JW.Jones SD.Murray CW.Franciskovich JB.Engel DB.Weber WW.Marimuthu J.Kyle JA.Smallwood JK.Farmen MW.Smith GF. Bioorg. Med. Chem. Lett. 2003, 13: 2255 - 9d
Shen M.LeTiran A.Xiao Y.Golbraikh A.Kohn H.Tropsha A. J. Med. Chem. 2002, 45: 2811 - 9e
Li Z.Yeo SL.Pallen CJ.Ganesan A. Bioorg. Med. Chem. Lett. 1998, 8: 2443 - 9f
Stewart AO.Bhatia PA.Martin JG.Summers JB.Rodriques KE.Martin MB.Holms JH.Moore JL.Craig RA.Kolasa T.Ratajczyk JD.Mazdiyasni H.Kerdesky FAJ.DeNinno SL.Maki RG.Bouska JB.Young PR.Lanni C.Bell RL.Carter GW.Brooks CDW. J. Med. Chem. 1997, 40: 1955 - 9g
Kohn H.Sawhney KN.Bardel P.Robertson DW.Leander JD. J. Med. Chem. 1993, 36: 3350 - 9h
Kohn H.Sawhney KN.LeGall P.Robertson DW.Leander JD. J. Med. Chem. 1991, 34: 2444 - 9i
Vansdadia RN.Roda KP.Parekh H. J. Indian Chem. Soc. 1989, 66: 110 - 9j
Kohn H.Sawhney KN.LeGall P.Conley JD.Robertson DW.Leander JD. J. Med. Chem. 1990, 33: 919 - 9k
Shah VH.Patel HH.Parikh AR. J. Indian Chem. Soc. 1982, 59: 678 - 10a
Hamann MT. Curr. Pharm. Des. 2003, 9: 879 - 10b
Liu YH.Bae BH.Alam N.Hong CJ.Lee CO.Im KS.Jung JH. J. Nat. Prod. 2001, 64: 1301 - 10c
Holler U.Konig GM.Wright AD. J. Nat. Prod. 1997, 60: 832 - 10d
Mittra A.Yamashita M.Kawasaki I.Murai H.Yoshioka T.Ohta S. Synlett 1997, 909 - 10e
Andrade R.Ayer WA.Trofinov LS. Aust. J. Chem. 1997, 50: 255 - 10f
Hedge VR.Patel MG.Das PR.Pramanik B.Puar MS. J. Antibiot. 1997, 50: 126 - 10g
Martinez A.Duque C.Sato N.Fujimoto Y. Chem. Pharm. Bull. 1997, 45: 181 - 10h
Rochfort SJ.Atkin D.Hobbs L.Capon RJ. J. Nat. Prod. 1996, 59: 1024 - 10i
Tait BD.Domagale J.Ellsworth EL.Ferguson D.Gajda C.Hupe D.Lunney EA.Tummino PJ. J. Mol. Recognit. 1996, 9: 139 - 10j
Romires KR.Chrusciel RA. Curr. Med. Chem. 1995, 2: 825 - 10k
Roggo BE.Petersen F.Delmendo R.Jenny HB.Peter HH.Roesel J. J. Antibiot. 1994, 47: 136 - 11
Greenhill JV.Ramli M.Tomassini T. J. Chem. Soc., Perkin Trans. 1 1975, 588 - 12a
Mack RA.Baer JE.Radov LA.Elzer PH.Georgiev VS. Eur. J. Med. Chim. Ther. 1989, 24: 61 - 12b
Hiyama T.Oishi H.Suetsugu Y.Nishide K.Saimoto H. Bull. Chem. Soc. Jpn. 1987, 60: 2139 - 12c
Mack RA.Georgiev VS.DeCory LA.Radov LA. Eur. J. Med. Chim. Ther. 1987, 22: 521 - 12d
Georgiev VS.Mack RA.Walter DJ.Radov LA.Baer JE. Helv. Chim. Acta 1987, 70: 1526