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Sulfamic acid as energy efficient catalyst for synthesis of flurophores, 1-H-spiro [isoindoline-1,2′-quinazoline]-3,4′(3′H)-diones

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Abstract

An energy efficient synthesis of 1-H-spiro[isoindoline-1,2 -quinazoline]-3,4 (3 H)-diones has been expediently accomplished by a reaction of isatin(s) / cyclic ketone and anthranilamide in ethanol at ambient temprature. Excellent yields of the products in short time duration, operational simplicity, and simple work-up procedure are the attractive features of the present protocol. Synthesized 1-H-spiro[isoindoline-1,2 -quinazoline]-3,4 (3 H)-diones were found to be fluorescent with absorption in UV region (302, 362 nm) and emission in visible region (413-436 nm) with Stokes shift of 44-72 nm.

Synthesis of 1-H-spiro [isoindoline-1,2’-quinazoline]-3,4’(3’H)-diones

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References

  1. Verdel B M, Souverein P C, Egberts A C G and Leufkens H G M 2006 Ann. Pharm. 40 1040

    CAS  Google Scholar 

  2. Bonola G, Da Re P, Magistretti M J, Massarani E and Setnikar I 1968 J. Med. Chem. 11 1136

    Article  CAS  Google Scholar 

  3. Russel H E and Alaimo R J 1972 J. Med. Chem. 15 335

    Article  Google Scholar 

  4. Kuo S C H, Lee Z, Juang J P, Lin Y T, Wu T S, Chang J J, Lednicer D, Paull K D, Lin C M, Hamel E and Lee K H 1993 J. Med. Chem. 36 1146

    Article  CAS  Google Scholar 

  5. Levin J I, Chan P S, Bailey T, Katocs A S and Venkatesan A M 1994 Bioorg. Med. Chem. Lett. 4 1141

    Article  CAS  Google Scholar 

  6. Hour M J, Huang L J, Kuo S C, Xia Y, Bastow K, Nakanishi Y, Hamel E and Lee K H 2000 J. Med. Chem. 43 4479

    Article  CAS  Google Scholar 

  7. Xu Z, Zhang Y, Fu H, Zhong H, Hong K and Zhu W 2011 Bioorg. Med. Chem. Lett. 21 4005

    Article  CAS  Google Scholar 

  8. Edmondson S, Danishefsky S, Sepp-lorenzinol L and Rosen N 1999 J. Am.Chem. Soc. 121 2147

    Article  CAS  Google Scholar 

  9. Laird A D, Vajkoczy P, Shawver L K, Thurnher A, Liang C, Mohammadi M, Schlessinger J, Ullrich A, Hubbard S R, Blake R A, Fong T A T, Strawn L M, Sun L, Tang C, Hawtin R, Tang F, Shenoy N, Hirth K P, McMahon G and Cherrington J M 2000 Cancer Research 60 4152

    CAS  Google Scholar 

  10. Fong T A T, Shawver L K, Sun L, Tang C, App H, Powell T J, Kim Y H, Schreck R, Wang X, Risau W, Ullrich A, Hirth K P and McMahon G 1999 Cancer Research 59 99

    CAS  Google Scholar 

  11. Mendel D B, Laird A D, Smolich B D, Blake R A, Liang C, Hannah A L, Shaheen R M, Ellis L, Weitman M S, Shawver L K and Cherrington J M 2000 Drug Design 15 29

    CAS  Google Scholar 

  12. Sun L, Tran N, Liang C, Hubbard S, Tang F, Lipson K, Schreck R, Zhou Y, McMahon G and Tang C 2000 J. Med. Chem. 43 2655

    Article  CAS  Google Scholar 

  13. Rambabu D, Raja G, Yogi Sreenivas B, Seerapu G P K, Lalith Kumar K, Si D. G, Haldar D I, Rao M V B and Pal M 2013 Bioorg. Med. Chem. Lett. 23 1351

    Article  CAS  Google Scholar 

  14. Lack N A, Axerio-Cilies P, Tavassoli P, Han F G, Chan K H, Feau C, LeBlanc E, Guns E T, Guy R K, Rennie P S and Cherkasov A 2011 J. Med. Chem. 54 8563

    Article  CAS  Google Scholar 

  15. Arya K and Dandia A 2007 Lett. Org. Chem. 4 378

    Article  CAS  Google Scholar 

  16. Sharma S D and Kaur V 1989 Synthesis 677

  17. Qiao R Z, Xu B L and Wang Y H 2007 Chin. Chem. Lett. 18 656

    Article  CAS  Google Scholar 

  18. Cai G P, Xu X L and Li Z F 2002 J. Heterocycl. Chem. 39 1271

    Article  CAS  Google Scholar 

  19. Asakawa H and Matano M 1979 Chem. Pharm. Bull. 27 1287

    Article  CAS  Google Scholar 

  20. Connolly D J, Cusack D, O’sullivan T P and Guiry P J 2005 Tetrahedron 61 10153

    Article  CAS  Google Scholar 

  21. Su W K and Yang B B 2002 Aust. J. Chem. 55 695

    Article  CAS  Google Scholar 

  22. Shi D Q, Rong L C and Wang J X 2004 Chem. J. Chin. Univ. 25 2051

    CAS  Google Scholar 

  23. Shi D Q, Wang J X and Rong L C 2003 J. Chem. Res. Synop. 671

  24. Shi D Q, Rong L C and Wang J X 2003 Tetrahedron Lett. 44 3199

    Article  CAS  Google Scholar 

  25. Shi D Q, Shi C L and Wang J X 2005 J. Heterocycl. Chem. 40 173

    Article  Google Scholar 

  26. Shaabani A, Maleki A and Mofakham H 2008 Synth. Commun. 38 3751

    Article  CAS  Google Scholar 

  27. Chen J X, Su W K and Wu H Y 2007 Green Chem. 9 972

    Article  CAS  Google Scholar 

  28. Hsu H, Tseng C C, Matii B and Sun C M 2012 Mol. Divers 16 241

    Article  CAS  Google Scholar 

  29. Rostami A, Tahmasbi B, Gholami H and Taymorian H 2013 Chin. Chem. Lett. 24 211

    Article  CAS  Google Scholar 

  30. Mohammadi A A, Dabiri M and Qaraat H 2009 Tetrahedron 65 3804

    Article  CAS  Google Scholar 

  31. Kefayati H, Vazifeh M and Kazemi-Rad R 2013 J. Chin. Chem. Soc. 60 1197

    CAS  Google Scholar 

  32. Narasimhulu M and Lee Y R 2011 Tetrahedron 67 9627

    Article  CAS  Google Scholar 

  33. Hu Y, Wang M M, Chen H and Shi D Q 2011 Tetrahedron 67 9342

    Article  CAS  Google Scholar 

  34. Bergman J, Engqvist R, Stalhandskec C and Wallbergd H 2003 Tetrahedron 59 1033

    Article  CAS  Google Scholar 

  35. Jiang Y, Liu Y, Tu S J and Shi F 2013 Tetrahedron: Asymmetry 24 1286

    Article  CAS  Google Scholar 

  36. Dabiri M, Mohammadi A A and Qaraat H 2009 Monatsh. Chem. 140 401

    Article  CAS  Google Scholar 

  37. Rambabu D, Kiran Kumar S, Sreenivas B Y, Sandra S, Kandale A, Misra P, Basaveswara Rao M V and Pal M 2013 Tetrahedron Lett. 54 495

    Article  CAS  Google Scholar 

  38. Varma R S 1999 Green Chem. 1 43

    Article  CAS  Google Scholar 

  39. Heravi M M, Baghernejad B and Oskooie H A 2009 Curr. Org. Chem. 13 1002

    Article  CAS  Google Scholar 

  40. Heravi M M, Alinejhad H and Bakhtiari K 2010 Mol. Divers. 14 621

    Article  CAS  Google Scholar 

  41. Li J P, Qiu J K and Li H 2011 J. Chin. J. Chem. 29 511

    Article  CAS  Google Scholar 

  42. Mane M M and Pore D M 2014 Tetrahedron Lett. 55 6601

    Article  CAS  Google Scholar 

  43. Hegade P G, Mane M M, Patil J D and Pore D M 2014 Synth. Commun. 1 1

    Google Scholar 

  44. Mane M M and Pore D M 2015 Synth. Commun. 1 868

    Article  Google Scholar 

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Acknowledgements

Authors DMP and MMM are thankful to UGC, New Delhi for financial assistance [F. No.42-394/2013 (SR)] and teacher fellowship under FDP [F.No-36-50/11WRO 30/12/2012], respectively.

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Correspondence to DATTAPRASAD M PORE.

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Supplementary Information (SI)

Experimental details, procedures and spectral data viz., IR, 1H, 13C NMR and Mass spectra of synthesized compounds are provided as supplementary file. Supplementary information is available at www.ias.ac.in/chemsci.

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MANE, M.M., PORE, D.M. Sulfamic acid as energy efficient catalyst for synthesis of flurophores, 1-H-spiro [isoindoline-1,2′-quinazoline]-3,4′(3′H)-diones. J Chem Sci 128, 657–662 (2016). https://doi.org/10.1007/s12039-016-1047-7

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  • DOI: https://doi.org/10.1007/s12039-016-1047-7

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