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A High Yielding, One-pot Synthesis of Substituted Ureas from the Corresponding Amines Using Mitsunobu’s Reagent

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Summary.

A Mitsunobu-based protocol has been developed for the synthesis of symmetrically and unsymmetrically substituted ureas from a variety of primary and secondary amines using gaseous carbon dioxide, in good to excellent yields. This protocol is mild and efficient compared to other reported methods.

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References

  • R Jayakumar S Nanjundan M Prabaharan (2006) Reactive and Functional Polymers 66 299 Occurrence Handle10.1016/j.reactfunctpolym.2004.12.008 Occurrence Handle1:CAS:528:DC%2BD28XitVKju7Y%3D

    Article  CAS  Google Scholar 

  • PYS Lam PK Jadhav CJ Eyermann CN Hodge Y Ru LT Bacheler JL Meek MJ Otto MM Rayner YN Wong CN Chang PC Weber DA Jackson TR Sharp S Erickson-Viitanen (1994) Science 263 380 Occurrence Handle10.1126/science.8278812 Occurrence Handle1:CAS:528:DyaK2cXitVOqtLg%3D

    Article  CAS  Google Scholar 

  • JB Schiere AJ Nell (1993) Animal Food Sci Technol 43 135 Occurrence Handle10.1016/0377-8401(93)90148-D

    Article  Google Scholar 

  • YS Chauhan A Apphun VK Singh BS Dwivedi (2004) Field Crops Res 89 17 Occurrence Handle10.1016/j.fcr.2004.01.016

    Article  Google Scholar 

  • A Abad J Lloveras A Michelena (2004) Field Crops Res 87 257 Occurrence Handle10.1016/j.fcr.2003.11.007

    Article  Google Scholar 

  • M Frezza S Castang J Estephane L Soulère C Deshayes B Chantegrel W Nasser Y Queneau S Reverchon A Doutheau (2006) Bioorg Med Chem 14 4781 Occurrence Handle10.1016/j.bmc.2006.03.017 Occurrence Handle1:CAS:528:DC%2BD28XltFOmtb4%3D

    Article  CAS  Google Scholar 

  • G Li LA Hasvold ZF Tao GT Wang SL Waltney SuffixII J Patel P Kovar RB Credo Z Chen H Zhang (2006) Bioorg Med Chem Lett 16 2293 Occurrence Handle10.1016/j.bmcl.2006.01.028 Occurrence Handle1:CAS:528:DC%2BD28Xitlaru78%3D

    Article  CAS  Google Scholar 

  • PYS Lam Y Ru PK Jhadhav PE Aldrich GV Delucca CJ Eyermann CH Chang G Emmett ER Holler WF Daneker RH Li JA Markwalder SP Seiz TR Sharpe LT Bacheler MM Rayner RM Klabe LY Shum DL Winslow DM Kornhauser DA Jackson S Erickson-Viitanen CN Hodge (1996) J Med Chem 39 3514 Occurrence Handle10.1021/jm9602571 Occurrence Handle1:CAS:528:DyaK28XkvVelsrc%3D

    Article  CAS  Google Scholar 

  • Hegarty AF, Drennan LJ (1995) In: Katrizky AR, Methocohn, O, Rees CW (eds) Comprehensive Organic Functional Group Transformations. Pergamon, Oxford, 6: 499

  • TP Vishnyakova EV Golubeva EV Glebova (1985) Russ Chem Rev 54 249 Occurrence Handle10.1070/RC1985v054n03ABEH003022

    Article  Google Scholar 

  • TW Greene PGM Wuts (1999) Protective Groups in Organic Synthesis EditionNumber3 John Wiley and Sons Inc. New York

    Google Scholar 

  • M Mensal M Gutschow (2005) Tetrahedron Lett 46 2231 Occurrence Handle10.1016/j.tetlet.2005.02.029

    Article  Google Scholar 

  • D Fattori PD Andrea M Porcelloni (2003) Tetrahedron Lett 44 811 Occurrence Handle10.1016/S0040-4039(02)02656-4 Occurrence Handle1:CAS:528:DC%2BD3sXptFShtw%3D%3D

    Article  CAS  Google Scholar 

  • S Curtet MM Langlois (1999) Tetrahedron Lett 40 8563 Occurrence Handle10.1016/S0040-4039(99)01817-1 Occurrence Handle1:CAS:528:DyaK1MXnsFSqs7c%3D

    Article  CAS  Google Scholar 

  • I Pri-Bar H Alper (1990) Can J Chem Rev Can Chem 68 1544 Occurrence Handle10.1139/v90-238 Occurrence Handle1:CAS:528:DyaK3cXmtlSktbs%3D

    Article  CAS  Google Scholar 

  • MB Smith J March (2001) Advanced Organic Chemistry EditionNumber5 SeriesTitleReactions, Mechanisms, and Structure Wiley Interscience New York, Chichester, Brisbane, Toronto, Singapore

    Google Scholar 

  • JS Nowick DL Holmes G Noronha EM Smith TM Nguyen SL Huang (1996) J Org Chem 61 3929 Occurrence Handle10.1021/jo960038n Occurrence Handle1:CAS:528:DyaK28XivFSgurc%3D

    Article  CAS  Google Scholar 

  • G Guichard V Semety C Didierjean A Asubry JP Briand M Rodriguez (1999) J Org Chem 64 8702 Occurrence Handle10.1021/jo990092e Occurrence Handle1:CAS:528:DyaK1MXmslSntbg%3D

    Article  CAS  Google Scholar 

  • RA Batey V Santhakumar C Yoshina-Ishii SD Taylor (1998) Tetrahedron Lett 39 6267 Occurrence Handle10.1016/S0040-4039(98)01330-6 Occurrence Handle1:CAS:528:DyaK1cXltlKnurc%3D

    Article  CAS  Google Scholar 

  • JE McCusker AD Main KS Johnson CA Grasso L McElwee-White (2000) J Org Chem 65 5216 Occurrence Handle10.1021/jo000364+ Occurrence Handle1:CAS:528:DC%2BD3cXlt1ent74%3D

    Article  CAS  Google Scholar 

  • A Bassoli B Rindone S Tollari F Chioccara (1990) J Mol Catal 60 41 Occurrence Handle10.1016/0304-5102(90)85065-P Occurrence Handle1:CAS:528:DyaK3cXlslWlsLY%3D

    Article  CAS  Google Scholar 

  • US Patent. 5902899, May 11, 1999

  • SP Gupte RV Chaudhuri (1988) J Catal 114 246 Occurrence Handle10.1016/0021-9517(88)90028-0 Occurrence Handle1:CAS:528:DyaL1MXhvFajtLs%3D

    Article  CAS  Google Scholar 

  • SAR Mulla CV Rode AA Kelkar SP Gupte (1997) J Mol Catal A Chem 122 103 Occurrence Handle10.1016/S1381-1169(97)00023-X Occurrence Handle1:CAS:528:DyaK2sXksVantbw%3D

    Article  CAS  Google Scholar 

  • A Basoli B Rindone S Tollari F Chioccara (1990) J Mol Catal 60 41 Occurrence Handle10.1016/0304-5102(90)85065-P

    Article  Google Scholar 

  • BD Dombeck R Angelici (1977) J Organomet Chem 134 203 Occurrence Handle10.1016/S0022-328X(00)81420-5

    Article  Google Scholar 

  • T Yoshida N Kambe S Murai N Sonoda (1986) Tetrahedron Lett 27 2037 Occurrence Handle10.1016/S0040-4039(00)84442-1

    Article  Google Scholar 

  • N Sonoda T Yasuhara K Kondo T Ikeda S Tsutsumi (1971) J Am Chem Soc 93 6344 Occurrence Handle10.1021/ja00752a099 Occurrence Handle1:CAS:528:DyaE38XkslCgsrs%3D

    Article  CAS  Google Scholar 

  • N Sonoda (1993) Pure Appl Chem 65 699 Occurrence Handle10.1351/pac199365040699 Occurrence Handle1:CAS:528:DyaK3sXitleisLg%3D

    Article  CAS  Google Scholar 

  • JE McCusker AD Main KS Johnson CA Grasso ME White (2000) J Org Chem 65 5216 Occurrence Handle10.1021/jo000364+ Occurrence Handle1:CAS:528:DC%2BD3cXlt1ent74%3D

    Article  CAS  Google Scholar 

  • JE McCusker F Qian L McElwee-White (2000) J Mol Catal A Chem 159 11 Occurrence Handle10.1016/S1381-1169(00)00164-3 Occurrence Handle1:CAS:528:DC%2BD3cXltVyltLo%3D

    Article  CAS  Google Scholar 

  • N Yamazaki F Hisaki T Iguchi (1974) Tetrahedron Lett 13 119

    Google Scholar 

  • Y Morimoto W Fujiwara H Taniguchi Y Hori Y Nagano (1986) Tetrahedron Lett 27 1809 Occurrence Handle10.1016/S0040-4039(00)84381-6 Occurrence Handle1:CAS:528:DyaL2sXjt1egsQ%3D%3D

    Article  CAS  Google Scholar 

  • CC Tai MJ Huck EP McKoon T Woo PG Jessop (2002) J Org Chem 67 9070 Occurrence Handle10.1021/jo026369j Occurrence Handle1:CAS:528:DC%2BD38XoslCjsLw%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 S Ray (2005) Lett Org Chem 2 742 Occurrence Handle10.2174/157017805774717472 Occurrence Handle1:CAS:528:DC%2BD28XhsVOjtA%3D%3D

    Article  CAS  Google Scholar 

  • D Chaturvedi S Ray (2005) J Sulfur Chem 26 365 Occurrence Handle10.1080/17415990500404848 Occurrence Handle1:CAS:528:DC%2BD28XkvFynsw%3D%3D

    Article  CAS  Google Scholar 

  • D Chaturvedi S Ray (2006) Monatsh Chem 137 201 Occurrence Handle10.1007/s00706-005-0417-5 Occurrence Handle1:CAS:528:DC%2BD28XotF2rsA%3D%3D

    Article  CAS  Google Scholar 

  • D Chaturvedi S Ray (2006) Monatsh Chem 137 311 Occurrence Handle10.1007/s00706-006-0438-8 Occurrence Handle1:CAS:528:DC%2BD28XitVCit70%3D

    Article  CAS  Google Scholar 

  • D Chaturvedi S Ray (2006) Monatsh Chem 137 459 Occurrence Handle10.1007/s00706-005-0452-2 Occurrence Handle1:CAS:528:DC%2BD28Xjt1KgtLs%3D

    Article  CAS  Google Scholar 

  • D Chaturvedi S Ray (2006) Monatsh Chem 137 465 Occurrence Handle10.1007/s00706-005-0460-2 Occurrence Handle1:CAS:528:DC%2BD28Xjt1Kgtbw%3D

    Article  CAS  Google Scholar 

  • D Chaturvedi S Ray (2006) J Sulfur Chem 27 265 Occurrence Handle10.1080/17415990600701697 Occurrence Handle1:CAS:528:DC%2BD28Xlt1Oit7Y%3D

    Article  CAS  Google Scholar 

  • D Chaturvedi S Ray (2006) Monatsh Chem 137 1219 Occurrence Handle10.1007/s00706-006-0514-0 Occurrence Handle1:CAS:528:DC%2BD28XptlOnsL4%3D

    Article  CAS  Google Scholar 

  • D Chaturvedi N Mishra V Mishra (2007) Monatsh Chem 138 57 Occurrence Handle10.1007/s00706-006-0557-2 Occurrence Handle1:CAS:528:DC%2BD2sXkslyn

    Article  CAS  Google Scholar 

  • D Chaturvedi N Mishra V Mishra (2006) Chin Chem Lett 17 1309 Occurrence Handle1:CAS:528:DC%2BD28Xht1ahtrrF

    CAS  Google Scholar 

  • D Chaturvedi N Mishra V Mishra (2007) J Sulfur Chem 28 39 Occurrence Handle10.1080/17415990601072262 Occurrence Handle1:CAS:528:DC%2BD2sXjs1amsLs%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 

  • D Chaturvedi S Ray (2006) Tetrahedron Lett 47 1307 Occurrence Handle10.1016/j.tetlet.2005.12.079 Occurrence Handle1:CAS:528:DC%2BD28XotFKiuw%3D%3D

    Article  CAS  Google Scholar 

  • D Chaturvedi S Ray (2007) Tetrahedron Lett 48 149 Occurrence Handle10.1016/j.tetlet.2006.10.149 Occurrence Handle1:CAS:528:DC%2BD28Xht1yktrfF

    Article  CAS  Google Scholar 

  • D Chaturvedi N Mishra V Mishra (2007) Tetrahedron Lett 48 5043 Occurrence Handle10.1016/j.tetlet.2007.05.103 Occurrence Handle1:CAS:528:DC%2BD2sXmvVKrsLY%3D

    Article  CAS  Google Scholar 

  • D Chaturvedi S Ray (2007) Current Org Chem 11 987 Occurrence Handle10.2174/138527207781058781 Occurrence Handle1:CAS:528:DC%2BD2sXot1Onsrw%3D

    Article  CAS  Google Scholar 

  • PA Enquest P Nilsson J Edin M Larhed (2005) Tetrahedron Lett 46 3335 Occurrence Handle10.1016/j.tetlet.2005.03.076

    Article  Google Scholar 

  • F Bigi B Frullanti R Maggi G Sartori E Zambonin (1999) J Org Chem 64 1004 Occurrence Handle10.1021/jo981109g Occurrence Handle1:CAS:528:DyaK1MXhslOlsQ%3D%3D

    Article  CAS  Google Scholar 

  • F Shi Y Deng T Sima H Yang (2001) Tetrahedron Lett 42 2161 Occurrence Handle10.1016/S0040-4039(01)00124-1 Occurrence Handle1:CAS:528:DC%2BD3MXhs1Ohur0%3D

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Medicinal and Process Chemistry Division, Central Drug Research Institute, Lucknow, U.P., India

    Devdutt Chaturvedi

  2. Synthetic Research Laboratory, Department of Chemistry, B.S.A. College, Mathura, U.P., India

    Nisha Mishra & Virendra Mishra

Authors
  1. Devdutt Chaturvedi
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  2. Nisha Mishra
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  3. Virendra Mishra
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Correspondence to Devdutt Chaturvedi.

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Chaturvedi, D., Mishra, N. & Mishra, V. A High Yielding, One-pot Synthesis of Substituted Ureas from the Corresponding Amines Using Mitsunobu’s Reagent. Monatsh Chem 139, 267–270 (2008). https://doi.org/10.1007/s00706-007-0776-1

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  • DOI: https://doi.org/10.1007/s00706-007-0776-1

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