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Monatshefte für Chemie - Chemical Monthly

, Volume 149, Issue 11, pp 2059–2067 | Cite as

The clean synthesis and confirmatory structural characterization of new 2-amino-4,8-dihydropyrano[3,2-b]pyran-3-cyano based on Kojic acid

  • Khadijeh Ojaghi Aghbash
  • Nader Noroozi Pesyan
  • Behrouz Notash
Original Paper
  • 77 Downloads

Abstract

A valuable and clean method was developed for the synthesis of the group of different novel 2-amino-4,8-dihydropyrano[3,2-b]pyran-3-carbonitriles containing a 2-aminopyran moiety by using of azido kojic acid and various 2-arylidinemalononitriles in the presence of NH4Cl as a catalyst in a green solvent (ethanol) with excellent yields. All structures were analyzed by FT-IR, 1H, 13C NMR spectroscopy, and representatively, one compound was analyzed by X-ray crystallography technique. Crystallographic analyses indicated that of this compound a dimer formed via two weak intermolecular hydrogen bonds with d(N···O) distances of 2.927 Å and made a 14-membered ring with centrosymmetric (Ci) form.

Graphical abstract

Keywords

Kojic acid Azido kojic acid Michael addition Pyran 2-Amino-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile 

Notes

Acknowledgements

We thank the Urmia University Research Council for supporting this work.

Supplementary material

706_2018_2254_MOESM1_ESM.pdf (3.3 mb)
Supplementary material 1 (PDF 3385 kb)

References

  1. 1.
    Green GR, Evans JM, Vong AK (1995) In: Katritzky AR, Rees CW, Scriven EFV (eds) Comprehensive heterocyclic chemistry II, vol 5. Pergamon Press, Oxford, p 469Google Scholar
  2. 2.
    Abe I, Oguro S, Utsumi Y, Sano Y, Noguchi H (2005) J Am Chem Soc 127:12709CrossRefPubMedGoogle Scholar
  3. 3.
    Sibi MP, Zimmerman J (2006) J Am Chem Soc 128:13346CrossRefPubMedPubMedCentralGoogle Scholar
  4. 4.
    Romdhane A, Jannet HB (2017) Arab J Chem 10:S3128CrossRefGoogle Scholar
  5. 5.
    Wang Y, Mo SY, Wang SJ, Li S, Yang YC, Shi JG (2005) Org Lett 7:1675CrossRefPubMedGoogle Scholar
  6. 6.
    Rajguru D, Keshwal BS, Jain S (2013) Med Chem Res 22:5934CrossRefGoogle Scholar
  7. 7.
    Parthasarathy K, Praveen C, Balachandran C, Ignacimuthu S, Perumal PT (2013) Bioorg Med Chem Lett 23:2708CrossRefPubMedGoogle Scholar
  8. 8.
    Wang S, Milne GW, Yan X, Posey IJ, Nicklaus MC, Graham L, Rice WG (1996) J Med Chem 39:2047CrossRefPubMedGoogle Scholar
  9. 9.
    Asghari S, Baharfar R, Alimi M, Ahmadipour M, Mohseni M (2014) Monatsh Chem 145:1337CrossRefGoogle Scholar
  10. 10.
    Hussain H, Aziz S, Schulz B, Krohn K (2011) Nat Prod Commun 6:841PubMedGoogle Scholar
  11. 11.
    He M, Yang N, Sun C, Yao X, Yang M (2011) Med Chem Res 20:200CrossRefGoogle Scholar
  12. 12.
    Schiller R, Tichotová L, Pavlík J, Buchta V, Melichar B, Votruba I, Kuneš J, Špulák M, Pour M (2010) Bioorg Med Chem Lett 20:7358CrossRefPubMedGoogle Scholar
  13. 13.
    Shahrisa A, Zirak M, Mehdipour AR, Miri R (2011) Chem Heterocycl Compd 46:1354CrossRefGoogle Scholar
  14. 14.
    Rideout JA, Smith IR, Sutherland MD (1976) Aust J Chem 29:1087CrossRefGoogle Scholar
  15. 15.
    Armesto D, Horspool WM, Martin N, Ramos A, Seoane C (1989) J Org Chem 54:3069CrossRefGoogle Scholar
  16. 16.
    Kumar D, Reddy VB, Sharad S, Dube U, Kapur S (2009) Eur J Med Chem 44:3805CrossRefPubMedGoogle Scholar
  17. 17.
    Hafez EA, Elnagdi MH, Elagamey AA, El-Taweel FA (1987) Heterocycles 26:903CrossRefGoogle Scholar
  18. 18.
    Lazzeri AL, Lapi E (1960) Bull Chim Farm 99:583Google Scholar
  19. 19.
    Banitaba SH, Safari J, Khalili SD (2013) Ultrason Sonochem 20:401CrossRefPubMedGoogle Scholar
  20. 20.
    Piao MZ, Imafuku K (1997) Tetrahedron Lett 38:5301CrossRefGoogle Scholar
  21. 21.
    Azimi R, Baharfar R (2014) Can J Chem 92:1163CrossRefGoogle Scholar
  22. 22.
    Chen C, Lu M, Liu Z, Wan J, Tu Z, Zhang T, Yan M (2013) Open J Med Chem 3:128CrossRefGoogle Scholar
  23. 23.
    Brahmachari G, Banerjee B (2013) ACS Sustain Chem Eng 2:411CrossRefGoogle Scholar
  24. 24.
    Bonsignore L, Loy G, Secci D, Calignano A (1993) Eur J Med Chem 28:517CrossRefGoogle Scholar
  25. 25.
    Kemnitzer W, Drewe J, Jiang S, Zhang H, Crogan-Grundy C, Labreque D, Bubenick M, Attardo G, Denis R, Lamothe S, Gourdeau H (2008) J Med Chem 51:417CrossRefPubMedGoogle Scholar
  26. 26.
    Kemnitzer W, Jiang S, Wang Y, Kasibhatla S, Crogan-Grundy C, Bubenik M, Labrecque D, Denis R, Lamothe S, Attardo G, Gourdeau H (2008) Bioorg Med Chem Lett 18:603CrossRefPubMedGoogle Scholar
  27. 27.
    Liao SY, Qian L, Miao TF, Shen Y, Zheng KC (2009) J Theor Comput Chem 8:143CrossRefGoogle Scholar
  28. 28.
    Foloppe N, Fisher LM, Howes R, Potter A, Robertson AG, Surgenor AE (2006) Bioorg Med Chem 14:4792CrossRefPubMedGoogle Scholar
  29. 29.
    Lu X, Dong Q, Dong X, Zhao W (2015) Tetrahedron 71:4061CrossRefGoogle Scholar
  30. 30.
    Bentley R (2006) Nat Prod Rep 23:1046CrossRefPubMedGoogle Scholar
  31. 31.
    Mohamad R, Mohamed MS, Suhaili N, Salleh MM, Ariff AB (2010) Biotechnol Mol Biol Rev 5:24Google Scholar
  32. 32.
    Zirak M, Eftekhari-Sis B (2015) Turk J Chem 39:439CrossRefGoogle Scholar
  33. 33.
    Noh JM, Kwak SY, Kim DH, Lee YS (2007) Pept Sci 88:300CrossRefGoogle Scholar
  34. 34.
    Ahn SM, Rho HS, Baek HS, Joo YH, Hong YD, Shin SS, Park YH, Park SN (2011) Bioorg Med Chem Lett 21:7466CrossRefPubMedGoogle Scholar
  35. 35.
    Rho HS, Baek HS, Ahn SM, Kim DH, Chang IS (2008) Bull Korean Chem Soc 29:1569CrossRefGoogle Scholar
  36. 36.
    Aytemir MD, Çaliş Ü, Oezalp M (2004) Arch Pharm 337:281CrossRefGoogle Scholar
  37. 37.
    Kim DH, Hwang JS, Baek HS, Kim KJ, Lee BG, Chang I, Kang HH, Lee OS (2003) Chem Pharm Bull 51:113CrossRefPubMedGoogle Scholar
  38. 38.
    Rho HS, Ahn SM, Yoo DS, Kim MK, Cho DH, Cho JY (2010) Bioorg Med Chem Lett 20:6569CrossRefPubMedGoogle Scholar
  39. 39.
    Novotný L, Rauko P, Abdel-Hamid M, Váchalková A (1999) Neoplasma 46:89PubMedGoogle Scholar
  40. 40.
    Aytemir MD, Özçelik B (2010) Eur J Med Chem 45:4089CrossRefPubMedGoogle Scholar
  41. 41.
    Reddy BS, Reddy MR, Madan CH, Kumar KP, Rao MS (2010) Bioorg Med Chem Lett 20:7507CrossRefPubMedGoogle Scholar
  42. 42.
    Saraei M, Ghasemi Z, Dehghan G, Hormati M, Ojaghi K (2017) Monatsh Chem 148:917CrossRefGoogle Scholar
  43. 43.
    Cho JC, Rho HS, Baek HS, Ahn SM, Woo BY, Hong YD, Cheon JW, Heo JM, Shin SS, Park YH, Suh KD (2012) Bioorg Med Chem Lett 22:2004CrossRefPubMedGoogle Scholar
  44. 44.
    Liju W, Ablajan K, Jun F (2015) Ultrason Sonochem 22:113CrossRefPubMedGoogle Scholar
  45. 45.
    Tu XJ, Fan W, Hao WJ, Jiang B, Tu SJ (2014) ACS Comb Sci 16:647CrossRefPubMedGoogle Scholar
  46. 46.
    Shestopalov AA, Rodinovskaya LA, Shestopalov AM, Litvinov VP (2004) Russ Chem Bull 53:724CrossRefGoogle Scholar
  47. 47.
    Teimuri-Mofrad R, Esmati S, Rabiei M, Gholamhosseini-Nazari M (2017) Heterocycl Commun 23:439CrossRefGoogle Scholar
  48. 48.
    Molaei HR, Sadeghi B, Moslemin MH (2017) Bulg Chem Commun 49:308Google Scholar
  49. 49.
    Tabassum S, Govindaraju S, Pasha MA (2015) Ultrason Sonochem 24:1CrossRefPubMedGoogle Scholar
  50. 50.
    Asghari S, Mohammadnia M (2017) Inorg Nanomet Chem 47:1004Google Scholar
  51. 51.
    Kataev EA, Reddy MR, Reddy GN, Reddy VH, Reddy CS, Reddy BV (2016) New J Chem 40:1693CrossRefGoogle Scholar
  52. 52.
    Baghbanian SM, Rezaei N, Tashakkorian H (2013) Green Chem 15:3446CrossRefGoogle Scholar
  53. 53.
    Moafi L, Ahadi S, Bazgir A (2010) Tetrahedron Lett 51:6270CrossRefGoogle Scholar
  54. 54.
    Xiong X, Pirrung C (2008) Org Lett 10:1151CrossRefPubMedGoogle Scholar
  55. 55.
    Rostamnia S, Zeynizadeh B, Doustkhah E, Baghban A, Aghbash KO (2015) Catal Commun 68:77CrossRefGoogle Scholar
  56. 56.
    Fakih S, Podinovskaia M, Kong X, Collins HL, Schaible UE, Hider RC (2008) J Med Chem 51:4539CrossRefPubMedGoogle Scholar
  57. 57.
    Durden JA, Stansbury HA, Catlette WH (1964) J Chem Eng Data 9:228CrossRefGoogle Scholar
  58. 58.
    Baharfar R, Azimi R (2014) Synth Commun 44:89CrossRefGoogle Scholar
  59. 59.
    Hasaninejad A, Shekouhy M, Golzar N, Zare A, Doroodmand MM (2011) Appl Catal A 402:11CrossRefGoogle Scholar
  60. 60.
    Adamson J, Coe BJ, Grassam HL, Jeffery JC, Coles SJ, Hursthouse MB (1999) J Chem Soc Perkin Trans 1(17):2483CrossRefGoogle Scholar
  61. 61.
    Steiner T (2002) Angew Chem Int Ed 41:48CrossRefGoogle Scholar
  62. 62.
    Kashani E, Noroozi Pesyan N, Rashidnejad H, Marjani AP, Asl HY (2017) J Iran Chem Soc 14:2143CrossRefGoogle Scholar
  63. 63.
    Stoe & Cie GmbH (2005) X-AREA. Version 1.31. Stoe & Cie GmbH, Darmstadt, GermanyGoogle Scholar
  64. 64.
    Sheldrick GM (1997) SHELXS97 and SHELXL97. University of Göttingen, GermanyGoogle Scholar

Copyright information

© Springer-Verlag GmbH Austria, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Department of Organic Chemistry, Faculty of ChemistryUrmia UniversityUrmiaIran
  2. 2.Department of Chemistry, Faculty of ScienceShahid Beheshti UniversityTehranIran

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