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A High Yielding, One-Pot, Triton-B Catalyzed, Expeditious Synthesis of Carbamate Esters by Four Component Coupling Methodology

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Summary.

A novel process for the one-step chemoselective conversion of alkyl halides into carbamates as protected amines was developed using benzyltrimethylammonium hydroxide (Triton-B) in presence of gaseous carbon dioxide. Thus, carbamate esters of different amines were prepared in very good to excellent yields.

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References

  • a) Adams P, Baron FA (1965) Chem Rev 65: 567; b) Mateen A, Chapalamadugu S, Kashar B, Bathi AR, Chaudhary GR (1994) Biol Degrad Biorem Toxic Chem 198; c) Wigfield YY (1996) Food Science Technol (NY) 77: 1501

  • a) Ray S, Chaturvedi D (2004) Drugs of the Future 29: 343; b) Ray S, Pathak SR, Chaturvedi D (2005) Drugs of the Future 30: 161

    Google Scholar 

  • a) Snieckus V (1990) Chem Rev 90: 879; b) Cleraland WW, Andrews TS, Gutteridge S, Hartman FC, Lorimer GH (1998) Chem Rev 98: 549; c) Tanaka F (2002) Chem Rev 102: 4885

  • Greene TW, Wuts PGM (1999) Protecting Groups in Organic Synthesis 3rd ed. John Wiley and Sons, Inc.; New York, 503

  • a) Mayer JP, Lewis GS, Curtius MJ, Zhang J (1997) Tetrahedron Lett 38: 8445; b) Buchstaller HP (1998) Tetrahedron 54: 3465; c) Holte PT, Thijs L, Zwanenburg B (1998) Tetrahedron Lett 39: 7404

  • a) Matsui T, Kondo T, Nishita Y, Itadani S, Tsuruta H, Fujita S, Omawari N, Sakai M, Nakazawa S, Ogata A, Mori H, Ohno H, Obata T, Nakai H, Toda M (2002) Bioorg Med Chem Lett 12: 907; b) Seko T, Kato M, Kohno H, Ono S, Hashimura K, Takimizu H, Nakai K, Maegawa H, Katsube N, Toda M (2002) Bioorg Med Chem Lett 12: 915

    Google Scholar 

  • DPN Satchell RS Satchell (1975) Chem Soc Rev 4 231 Occurrence Handle10.1039/cs9750400231 Occurrence Handle1:CAS:528:DyaE2MXkvFGktr0%3D

    Article  CAS  Google Scholar 

  • S Raucher DS Jones (1985) Synth Commun 15 1025 Occurrence Handle1:CAS:528:DyaL28XitVKgsro%3D

    CAS  Google Scholar 

  • a) Leung TW, Domblk BD (1992) Chem Commun 3: 205; b) Mizuno T, Takahashi J, Ogawa A (2002) Tetrahedron 58: 7805

  • a) Chaturvedi D, Kumar A, Rastogi R, Srivastava AK, Tewari P, Ahmad R, Chander R, Puri A, Bhatia G, Rizvi F, Rastogi AK, Ray S (2004) US Patent 2004192688; CAN 141: 2955752; b) Chaturvedi D, Kumar A, Rastogi R, Srivastava AK, Tewari P, Ahmad R, Chander R, Puri A, Bhatia G, Rizvi F, Rastogi AK, Ray S (2005) PCT Int. Appl. WO2005042465; CAN 142: 463462; c) Chaturvedi D, Srivastava AK, Chander R, Ray S. Bioorganic Medicinal Chemistry, Manuscript Submitted

  • a) Casedei MA, Inesi A, Moracci FM, Rossi L (1996) Chem Commun 2575; b) Casadei MA, Moracci FM, Zappia G, Inesi A, Rossi L (1997) J Org Chem 62: 6754; c) Feroci M, Inesi A, Rossi L (2000) Tetrahedron Lett 41: 963

  • MA Yoshida N Hara S Okuyama (2000) Chem Commun 2 151

    Google Scholar 

  • R Mahe Y Sasaki C Bruneau PH Dixneuf (1989) J Org Chem 54 1518 Occurrence Handle10.1021/jo00268a008 Occurrence Handle1:CAS:528:DyaL1MXhsFektrw%3D

    Article  CAS  Google Scholar 

  • D Chaturvedi A Kumar S Ray (2002) Synth Commun 32 2651 Occurrence Handle10.1081/SCC-120006028 Occurrence Handle1:CAS:528:DC%2BD38XmslCrs7w%3D

    Article  CAS  Google Scholar 

  • D Chaturvedi A Kumar S Ray (2003) Tetrahedron Lett 44 7637 Occurrence Handle10.1016/j.tetlet.2003.08.018 Occurrence Handle1:CAS:528:DC%2BD3sXnt1yitrc%3D

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Medicinal & Process Chemistry Division, Central Drug Research Institute, 226001, Lucknow, India

    Devdutt Chaturvedi & S. Ray

Authors
  1. Devdutt Chaturvedi
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  2. S. Ray
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Correspondence to Devdutt Chaturvedi.

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Present address: Institute of Organic and Biomolecular Chemistry, George–August University, 37077, Göttingen, Germany

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Chaturvedi, D., Ray, S. A High Yielding, One-Pot, Triton-B Catalyzed, Expeditious Synthesis of Carbamate Esters by Four Component Coupling Methodology. Monatsh. Chem. 137, 201–206 (2006). https://doi.org/10.1007/s00706-005-0417-5

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  • DOI: https://doi.org/10.1007/s00706-005-0417-5

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