RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000083.xml
PDF herunterladen
Synlett 2011(16): 2335-2338
DOI: 10.1055/s-0030-1261222
DOI: 10.1055/s-0030-1261222
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New YorkFacile One-Pot Synthesis of Carbamoylbenzotriazoles Directly from CO2: Synthesis of Tolbutamide
Weitere Informationen
Received
8 June 2011
Publikationsdatum:
08. September 2011 (online)
Publikationsverlauf
Publikationsdatum:
08. September 2011 (online)
Abstract
CO2 gas trapped with a primary or secondary amine as a carbamate salt in the presence of DBU reacts with triphenylphosphine and 1-chlorobenzotriazole (BtCl) to form a carbamoylbenzotriazole urea, which reacts with para-toluenesulfonamide under solvent-free conditions to produce N-sulfonyl ureas such as tolbutamide.
Key words
CO2 - BtCl - Bt urea - sulfonyl urea - tolbutamide
- Supporting Information for this article is available online:
- Supporting Information
- 1a
Arakawa H.Aresta M.Armor JN.Barteau MA.Beckman EJ.Bell AT.Bercaw JE.Creutz C.Dinjus E.Dixon DA.Domen K.DuBois DL.Eckert J.Fujita E.Gibson DH.Goddard WA.Goodman DW.Keller J.Kubas GJ.Kung HH.Lyons JE.Manzer LE.Marks TJ.Morokuma K.Nicholas KM.Periana R.Que L.Rostrup-Nielson J.Sachtler WM.Schmidt LD.Sen A.Somorjai GA.Stair PC.Stults BR.Tumas W. Chem. Rev. 2001, 101: 953MissingFormLabel - 1b
Rudkevich DM.Xu H. Chem. Commun. 2005, 2651MissingFormLabel - 2a
Artuso E.Degani I.Fochi R.Magistris C. Synthesis 2007, 3497MissingFormLabel - 2b
Degani I.Fochi R.Magistris C. Synthesis 2009, 3807MissingFormLabel - 3a
Aresta M.Quaranta E. Tetrahedron 1992, 48: 1515MissingFormLabel - 3b
McGhee WD.Pan Y.Riley DP. J. Chem. Soc., Chem. Commun. 1994, 699MissingFormLabel - 3c
McGhee WD.Riley PD.Christ K.Pan Y.Parnas B.Company M.Boulevard NL.Louis S. J. Org. Chem. 1995, 60: 2820MissingFormLabel - 4a
Salvatore RN.Shin SI.Nagle AS.Jung KW.
J. Org. Chem. 2001, 66: 1035MissingFormLabel - 4b
Salvatore RN.Chu F.Nagle AS.Kapxhiu EA.Cross RM.Jung KW. Tetrahedron 2002, 58: 3329MissingFormLabel - 5
Nomura R.Hasegawa Y.Ishimoto M.Toyosaki T.Matsuda H. J. Org. Chem. 1992, 57: 7339 - 6
Saylik D.Horvath MJ.Elmes PS.Jackson WR.Lovel CG.Moody K. J. Org. Chem. 1999, 64: 3940 - 7
McGhee WD.Pan Y.Talley JJ. Tetrahedron Lett. 1994, 35: 839 - 8
Chaturvedi D.Mishra N.Mishra V. Synthesis 2008, 355 - 9
García-Egido E.Fernandez-Suarez M.Muñoz L. J. Org. Chem. 2008, 73: 2909 - 10
García-Egido Paz J.Iglesias B.Muñoz L. Org. Biomol. Chem. 2009, 7: 3991 - 11
Katritzky AR.Chunming C.Sandeep KS. J. Org. Chem. 2006, 71: 3375 - 12
Katritzky AR.Pleynet DPM.Yang B. J. Org. Chem. 1997, 62: 4155 - 13
Katritzky AR.Monteux DA.Tymoshenko DO.Belyakov SA. J. Chem. Res., Synop. 1999, 230 - 14
Butula I.Vela V.Prostenik MV. Croat. Chem. Acta 1979, 52: 47 - 15a
Kecskemeti V.Bagi Z.Pacher P.Posa I.Kocsis E.Koltai MZ. Curr. Med. Chem. 2002, 9: 53MissingFormLabel - 15b
Sartori G.Maggi R. Science of Synthesis Vol. 18: Thieme; Stuttgart: 2005. p.665-758MissingFormLabel - 16
Mohamadi F.Spees M. J. Med. Chem. 1992, 35: 3012 - 17
Cervello J.Sastre T. Synthesis 1990, 221 - 18
Chibale K.Gessner RK. Synlett 2009, 2839 - 19
Luckhurst CA.Millichip I.Parker B.Reuberson J.Furber M. Tetrahedron Lett. 2007, 48: 8878 - 20
Rees CW.Storr RC. J. Chem. Soc., Chem. Commun. 1968, 1305