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Iron(III) Chloride mediated reduction of Bis(1-isoquinolylcarbonyl)amide to an Amide†

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Abstract

In methanol, FeCl3 reacted readily with L1H (L1H = bis(1-isoquinolylcarbonyl)amide) and afforded a complex having the formula [Fe(L2)Cl2] (1) {L2 − = N-((1-isoquinolyl)(methoxy)methyl)isoquinoline-1-carboxamide ion}. This reaction involves reduction of one of the two carbonyl groups present in L1H to (methoxy)methyl group. A plausible mechanism for the conversion of L1H to L2 − has been proposed. Determination of molecular structure of 1 confirmed this conversion. Fe(III) ion is surrounded by three nitrogen atoms of the ligand and two chloride ions, imparting a rare distorted trigonal bipyramidal N3Cl2 coordination environment.

In methanol, FeCl3 reacted with bis(1-isoquinolylcarbonyl)amide affording N-((1-isoquinolyl)(methoxy)methyl)isoquinoline-1-carboxamide bound iron(III) complex. This reaction involves reduction of one of the two carbonyl groups to (methoxy)methyl group.

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References

  1. Bolm C, Legros J, Le Paih J and Zani L 2004 Chem. Rev. 104 6217

    Article  CAS  Google Scholar 

  2. Plietker B 2008 In Iron Catalysis in Organic Chemistry: Reactions and Applications (Weinheim: Wiley- VCH)

  3. Stamatatos T C, Efthymiou C G, Stoumpos C and Perlepes S P 2009 Eur. J. Inorg. Chem. 3361

  4. Thirupathi P and Kim S S 2010 J. Org. Chem. 75 5240

    Article  CAS  Google Scholar 

  5. Csihony S, Mehdi S S, Homonnay Z, Vértes A, Farkas Ö and Horváth I T 2002 J. Chem. Soc., Dalton Trans. 680

  6. Kidwai M, Mishra N K, Bansal V, Kumar A and Mozumdar S 2009 Tetrahedron Lett. 50 1355

    Article  CAS  Google Scholar 

  7. Christoffers J 1997 Chem. Commun. 943

  8. Li H, Xu X, Yang J, Xie X, Huang H and Li Y 2011 Tetrahedron Lett. 52 530

    Article  CAS  Google Scholar 

  9. Anxionnat B, Guérinot A, Reymond S and Cossy J 2009 Tetrahedron Lett. 50 3470

    Article  CAS  Google Scholar 

  10. Niu T, Huang L, Wu T and Zhang Y 2011 Org. Biomol. Chem. 9 273

    Article  CAS  Google Scholar 

  11. Li R, Wang S R and Lu W 2007 Org. Lett. 9 2219

    Article  CAS  Google Scholar 

  12. Jenner B E L and Lindsey Jr. R V 1960 J. Am. Chem. Soc. 83 1911

    Article  Google Scholar 

  13. Yiu S, Wu Z, Mak C and Lau T 2004 J. Am. Chem. Soc. 126 14921

    Article  CAS  Google Scholar 

  14. Noda D, Sunada Y, Hatakeyama T, Nakamura M and Nagashima H 2009 J. Am. Chem. Soc. 131 6078

    Article  CAS  Google Scholar 

  15. Stoyanovsky D A, Clancy R and Cederbaum A I 1999 J. Am. Chem. Soc. 121 5093

    Article  CAS  Google Scholar 

  16. Trost B M and Ornstein P L 1983 J. Org. Chem. 48 1133

    Article  Google Scholar 

  17. Toda F, Tanaka K and Iwata S 1989 J. Org. Chem. 54 3007

    Article  CAS  Google Scholar 

  18. Wang J, Huang W, Zhang Z, Xiang X, Liu R and Zhou X 2009 J. Org. Chem. 74 3299

    Article  CAS  Google Scholar 

  19. Li R, Wang S R and Lu W 2007 Org. Lett. 9 2219

    Article  CAS  Google Scholar 

  20. Wang S, Wang Z and Zheng X 2009 Chem. Commun. 7372

  21. Chatterjee S K and Nuhn P 1998 Chem. Commun. 1729

  22. Liu C, Yang F, Jin Y, Ma X, Cheng D, Li N and Tian S 2010 Org. Lett. 12 3832

    Article  CAS  Google Scholar 

  23. Chu C, Huang W, Lu C, Wu P, Liu J and Yao C 2006 Tetrahedron Lett. 47 7375

    Article  CAS  Google Scholar 

  24. Iwanami K, Aoyagi M and Oriyama T 2005 Tetrahedron Lett. 46 7487

    Article  CAS  Google Scholar 

  25. Karamé I, Alamé M, Kanj A, Baydoun G N, Hazimeh H, Masri M and Christ L 2011 C. R. Chim. 14 525

    Article  Google Scholar 

  26. Elinson M N, Ilovaisky A I, Merkulova V M, Barba F and Batanero B 2008 Tetrahedron 64 5915

    Article  CAS  Google Scholar 

  27. Sahu R, Fulwa V K, Jena H S and Manivannan V 2012 Polyhedron 33 9

    Article  CAS  Google Scholar 

  28. Sahu R, Padhi S K, Jena H S and Manivannan V 2010 Inorg. Chim. Acta 363 1448

    Article  CAS  Google Scholar 

  29. Sheldrick G M 1996 SADABS, University of Göttingen, Gttingen, Germany

  30. SMART and SAINT, Siemens Analytical X-ray Instruments Inc., Madison, WI, 1996

  31. Sheldrick G M 2008 Acta. Cryst. A 64 112

    Article  CAS  Google Scholar 

  32. Ostendorf M, Romagnoli R, Cabeza Pereiro I C, Roos E C, Moolenaar M J, Speckamp W N and Hiemstra H 1997 Tetrahedron: Asymmetry 8 1773

    Article  CAS  Google Scholar 

  33. Wocadlo S, Massa W and Folgado J 1993 Inorg. Chim. Acta. 207 199

    Article  CAS  Google Scholar 

  34. Bedford R B, Bruce D W, Frost R M, Goodby J W and Hird M 2004 Chem. Commun. 2822

  35. Yamaguchi Y, Ando H, Nagaya M, Hinago H, Ito T and Asami M 2011 Chem. Lett. 40 983

    Article  CAS  Google Scholar 

  36. Addison A W, Rao T N, Reedijk J, van Rijn J and Verschor G C 1984 J. Chem. Soc. Dalton Trans. 1349

  37. Small B L, Brookhart M and Bennett A M A 1998 J. Am. Chem. Soc. 120 4049

    Article  CAS  Google Scholar 

  38. Britovsek G J P, Bruce M, Gibson V C, Kimberley B S, Maddox P J, Mastroianni S, McTavish S J, Redshaw C, Solan G A, Strömberg S, White A J P and Williams D J 1999 J. Am. Chem. Soc. 121 8728

    Article  CAS  Google Scholar 

  39. Mandon D, Machkour A, Goetz S and Welter R 2002 Inorg. Chem. 41 5364

    Article  CAS  Google Scholar 

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Acknowledgements

We are grateful to the Department of Science and Technology (DST), New Delhi, for financial grant and establishing the single crystal X-ray diffractometer facility under FIST scheme. The authors are thankful to Dr. Babulal Das for the X-ray data.

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Authors and Affiliations

  1. Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati, 781 039, India

    ROJALIN SAHU, PAPULI CHALIHA & VADIVELU MANIVANNAN

  2. School of Applied Sciences (Chemistry), Campus-3, KIIT UNIVERSITY, Patia, Bhubaneswar, 751 024, India

    ROJALIN SAHU

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  1. ROJALIN SAHU
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  2. PAPULI CHALIHA
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  3. VADIVELU MANIVANNAN
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Correspondence to VADIVELU MANIVANNAN.

Additional information

Dedicated to Professor Animesh Chakravorty on the occasion of his 80th birth anniversary.

Supplementary Information (SI)

CCDC number 987001 contains the supplementary crystallographic data for complex 1. This data can be obtained free of charge via http://www.ccdc.ac.uk/conts/retrieving.html or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: (+44) 1223-336-033; or e-mail: deposit@ccdc.cam.ac.uk. IR spectrum of 1 is provided which is available at www.ias.ac.in/chemsci.

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SAHU, R., CHALIHA, P. & MANIVANNAN, V. Iron(III) Chloride mediated reduction of Bis(1-isoquinolylcarbonyl)amide to an Amide† . J Chem Sci 128, 37–42 (2016). https://doi.org/10.1007/s12039-015-1001-0

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  • DOI: https://doi.org/10.1007/s12039-015-1001-0

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