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Facile solvent-free synthesis and structural elucidation of styrylcyclohex-2-enone derivatives

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Abstract

A remarkably efficient procedure for the synthesis of styrylcyclohex-2-enone derivatives at room temperature is described using a mild reaction medium consisting of lithium perchlorate and N-(trimethylsilyl)diethylamine. Several compounds of this class are synthesized conveniently and rapidly. Spectroscopic and X-ray diffraction experiments confirm the proposed structures.

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References

  • A Modzelewska C Pettit G Achanta NE Davidson P Huang SR Khan (2006) Bioorg Med Chem 14 3491 Occurrence Handle10.1016/j.bmc.2006.01.003 Occurrence Handle1:CAS:528:DC%2BD28XjtFGjurY%3D

    Article  CAS  Google Scholar 

  • SJ Won CT Liu LT Tsao JR Weng HH Ko JP Wang CN Lin (2005) Eur J Med Chem 40 103 Occurrence Handle10.1016/j.ejmech.2004.09.006 Occurrence Handle1:CAS:528:DC%2BD2MXjtF2jtA%3D%3D

    Article  CAS  Google Scholar 

  • S Kobayashi K Kakumoto M Sugiura (2002) Org Lett 4 1319 Occurrence Handle10.1021/ol0256163 Occurrence Handle1:CAS:528:DC%2BD38XitVOis7s%3D

    Article  CAS  Google Scholar 

  • Z Han S Uehira H Shinokubo K Oshima (2001) J Org Chem 66 7854 Occurrence Handle10.1021/jo016054o Occurrence Handle1:CAS:528:DC%2BD3MXns12lsLw%3D

    Article  CAS  Google Scholar 

  • R Brettle (1979) Aldehydes JF Stoddart (Eds) Comprehensive Organic Synthesis NumberInSeries1 Pergammon Press Oxford 963

    Google Scholar 

  • L Claisen (1899) Justus Liebigs Ann Chem 306 322 Occurrence Handle10.1002/jlac.18993060305 Occurrence Handle1:CAS:528:DyaD28Xps1OntQ%3D%3D

    Article  CAS  Google Scholar 

  • AT Nielsen WJ Houlihan (1968) Org React NumberInSeries16 John Wiley & Sons New York

    Google Scholar 

  • W Wang Y Mei H Li J Wang (2005) Org Lett 7 601 Occurrence Handle10.1021/ol047630g Occurrence Handle1:CAS:528:DC%2BD2MXktFersQ%3D%3D

    Article  CAS  Google Scholar 

  • G Deng T Ren (2003) Synth Commun 33 2995 Occurrence Handle10.1081/SCC-120022473 Occurrence Handle1:CAS:528:DC%2BD3sXmvFCnsbo%3D

    Article  CAS  Google Scholar 

  • X Wang S Cheng (2006) Catal Commun 7 689 Occurrence Handle10.1016/j.catcom.2006.02.021 Occurrence Handle1:CAS:528:DC%2BD28Xmt1GnsLc%3D

    Article  CAS  Google Scholar 

  • V Calvino M Picallo AJ López-Peinado RM Martín-Aranda CJ Durán-Valle (2006) Appl Surf Sci 252 6071 Occurrence Handle10.1016/j.apsusc.2005.11.006 Occurrence Handle1:CAS:528:DC%2BD28XmslChtr4%3D

    Article  CAS  Google Scholar 

  • P Formentín H García A Leyva (2004) J Mol Catal A Chem 214 137 Occurrence Handle10.1016/j.molcata.2003.05.001 Occurrence Handle1:CAS:528:DC%2BD2cXjtVentrw%3D

    Article  CAS  Google Scholar 

  • DB Ramachary K Ramakumar M Kishor (2005) Tetrahedron Lett 46 7037 Occurrence Handle10.1016/j.tetlet.2005.08.051 Occurrence Handle1:CAS:528:DC%2BD2MXpvVSms78%3D

    Article  CAS  Google Scholar 

  • AA Esmaeili MS Tabas MA Nasseri F Kazemi (2005) Monatsh Chem 136 571 Occurrence Handle10.1007/s00706-004-0256-9 Occurrence Handle1:CAS:528:DC%2BD2MXisl2qtr8%3D

    Article  CAS  Google Scholar 

  • F Fringuelli G Pani O Piermatti F Pizzo (1994) Tetrahedron 50 11499 Occurrence Handle10.1016/S0040-4020(01)89287-5 Occurrence Handle1:CAS:528:DyaK2MXhtFWlu7k%3D

    Article  CAS  Google Scholar 

  • Nivalkar KR, Mudaliar CD, Mashraqui SH (1992) J Chem Res:98

  • R Lemke (1970) Chem Ber 103 1168 Occurrence Handle10.1002/cber.19701030419 Occurrence Handle1:CAS:528:DyaE3cXhtlahsbw%3D

    Article  CAS  Google Scholar 

  • Y El Barkaoui N Jorio S Fakih-Tetouani A El Louzi A Loupy (1999) Heterocycles 51 1517 Occurrence Handle1:CAS:528:DyaK1MXks1KrsLk%3D Occurrence Handle10.3987/COM-98-8454

    Article  CAS  Google Scholar 

  • G Kabas (1965) Tetrahedron 22 1213 Occurrence Handle10.1016/S0040-4020(01)99412-8

    Article  Google Scholar 

  • RE Christ RC Fuson (1937) J Am Chem Soc 59 893 Occurrence Handle10.1021/ja01284a036 Occurrence Handle1:CAS:528:DyaA2sXjtVGqtA%3D%3D

    Article  CAS  Google Scholar 

  • Dewar J, Morrison DR, Read J (1936) J Chem Soc:1598

  • EK Fields RW Dunlap M Bruck A Podias HK Hall SuffixJr (1989) J Org Chem 54 2244 Occurrence Handle10.1021/jo00270a042 Occurrence Handle1:CAS:528:DyaL1MXitlWitL0%3D

    Article  CAS  Google Scholar 

  • Shu C-F, Tsai W-J, Chen J-Y, Jen AK-Y, Zhang Y, Chen T-A (1996) Chem Commun:2279

  • C-F Shu W-J Tsai AK-Y Jen (1996) Tetrahedron Lett 37 7055 Occurrence Handle10.1016/0040-4039(96)01550-X Occurrence Handle1:CAS:528:DyaK28XmtVGku7Y%3D

    Article  CAS  Google Scholar 

  • Wattanasin S, Murphy WS (1980) Synthesis:647

  • PK Chaudhuri (1990) Indian J Chem B 29 154

    Google Scholar 

  • S Suresh H Zengin BK Spraul T Sassa T Wada PrefixDr DW Smith (2005) Tetrahedron Lett 46 3913 Occurrence Handle10.1016/j.tetlet.2005.03.140 Occurrence Handle1:CAS:528:DC%2BD2MXjslyrt78%3D

    Article  CAS  Google Scholar 

  • PA Grieco JJ Nunes MD Gaul (1990) J Am Chem Soc 112 4595 Occurrence Handle10.1021/ja00167a096 Occurrence Handle1:CAS:528:DyaK3cXitlCntb0%3D

    Article  CAS  Google Scholar 

  • PA Grieco JD Clark CT Jagoe (1991) J Am Chem Soc 113 5488 Occurrence Handle10.1021/ja00014a069 Occurrence Handle1:CAS:528:DyaK3MXkvFWntLc%3D

    Article  CAS  Google Scholar 

  • MR Saidi N Azizi MR Naimi-Jamal (2001) Tetrahedron Lett 42 8111 Occurrence Handle10.1016/S0040-4039(01)01732-4 Occurrence Handle1:CAS:528:DC%2BD3MXnsl2qtb8%3D

    Article  CAS  Google Scholar 

  • S Sudha KM Narasimhan VG Saraswathy S Sankararaman (1996) J Org Chem 61 1877 Occurrence Handle10.1021/jo951839d Occurrence Handle1:CAS:528:DyaK28XhtFektLw%3D

    Article  CAS  Google Scholar 

  • KW Hunt PA Grieco (2001) Org Lett 3 481 Occurrence Handle10.1021/ol0003836 Occurrence Handle1:CAS:528:DC%2BD3MXksVOhtw%3D%3D

    Article  CAS  Google Scholar 

  • MR Saidi M Nazari (2004) Monatsh Chem 135 309 Occurrence Handle1:CAS:528:DC%2BD2cXhtlygtrY%3D

    CAS  Google Scholar 

  • Markert M, Mahrwald R (2004) Synthesis:1429

  • Gunanathan C (2002) Synlett:649

  • MM Mojtahedi H Abbasi MS Abaee B Mohebali (2006) Monatsh Chem 137 455 Occurrence Handle10.1007/s00706-005-0458-9 Occurrence Handle1:CAS:528:DC%2BD28Xjt1Kgtb4%3D

    Article  CAS  Google Scholar 

  • MR Saidi MM Mojtahedi M Bolourtchian (1997) Tetrahedron Lett 38 8071 Occurrence Handle10.1016/S0040-4039(97)10110-1 Occurrence Handle1:CAS:528:DyaK2sXnsV2gs70%3D

    Article  CAS  Google Scholar 

  • MR Naimi-Jamal MM Mojtahedi J Ipaktschi MR Saidi (1999) J Chem Soc Perkin Trans 1 3709 Occurrence Handle10.1039/a904498a

    Article  Google Scholar 

  • MM Mojtahedi MR Saidi JS Shirzi M Bolourtchian (2001) Synth Commun 31 3587 Occurrence Handle10.1081/SCC-100107005 Occurrence Handle1:CAS:528:DC%2BD3MXnvFCgurg%3D

    Article  CAS  Google Scholar 

  • Abaee MS, Mojtahedi MM, Zahedi MM (2005) Synlett:2317

  • MS Abaee MM Mojtahedi MM Zahedi M Bolourtchian (2006) Synth Commun 36 199 Occurrence Handle10.1080/00397910500334447 Occurrence Handle1:CAS:528:DC%2BD28Xkslelug%3D%3D

    Article  CAS  Google Scholar 

  • MS Abaee MM Mojtahedi R Sharifi MM Zahedi H Abbasi K Tabar-Heidar (2006) J Iran Chem Soc 3 293 Occurrence Handle1:CAS:528:DC%2BD28XhtVWhurbF

    CAS  Google Scholar 

  • MS Abaee MM Mojtahedi MM Zahedi R Sharifi (2007) Heteroatom Chem 18 44 Occurrence Handle10.1002/hc.20252 Occurrence Handle1:CAS:528:DC%2BD2sXpsVynug%3D%3D

    Article  CAS  Google Scholar 

  • MS Abaee MM Mojtahedi MM Zahedi R Sharifi AW Mesbah W Massa (2007) Synth Commun 37 2949 Occurrence Handle10.1080/07370650701471756 Occurrence Handle1:CAS:528:DC%2BD2sXpvVKqsLo%3D

    Article  CAS  Google Scholar 

  • Abaee MS, Mojtahedi MM, Zahedi MM, Sharifi R, Khavasi H (2007) Synthesis:3339

  • W Schroth U Jahn D Strohl (1994) Chem Ber 127 2013 Occurrence Handle10.1002/cber.19941271026 Occurrence Handle1:CAS:528:DyaK2MXpvF2lug%3D%3D

    Article  CAS  Google Scholar 

  • MR Saidi A Heidari J Ipaktschi (1994) Chem Ber 127 1761 Occurrence Handle10.1002/cber.19941270928 Occurrence Handle1:CAS:528:DyaK2MXovVKjuw%3D%3D

    Article  CAS  Google Scholar 

Download references

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Authors and Affiliations

  1. Organic Chemistry Laboratory, Chemistry and Chemical Engineering Research Center of Iran, Tehran, Iran

    Mohammad M. Mojtahedi, Mohammad Saeed Abaee, Mohammad Mehdi Zahedi, Mohammad R. Jalali & A. Wahid Mesbah

  2. Fachbereich Chemie der Philipps-Universitaet Marburg, Marburg, Germany

    Werner Massa

  3. Sari Center, Payam Noor University, Sari, Iran

    Roholah Yaghoubi & Mehdi Forouzani

Authors
  1. Mohammad M. Mojtahedi
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  2. Mohammad Saeed Abaee
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  3. Mohammad Mehdi Zahedi
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  4. Mohammad R. Jalali
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  5. A. Wahid Mesbah
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  6. Werner Massa
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  7. Roholah Yaghoubi
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  8. Mehdi Forouzani
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Corresponding author

Correspondence to Mohammad M. Mojtahedi.

Additional information

Correspondence: Mohammad M. Mojtahedi and Mohammad Saeed Abaee, Organic Chemistry Laboratory, Chemistry and Chemical Engineering Research Center of Iran, P.O. Box 14335-186, Tehran, Iran.

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Mojtahedi, M., Abaee, M., Zahedi, M. et al. Facile solvent-free synthesis and structural elucidation of styrylcyclohex-2-enone derivatives. Monatsh Chem 139, 917–921 (2008). https://doi.org/10.1007/s00706-007-0847-3

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  • DOI: https://doi.org/10.1007/s00706-007-0847-3

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