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.
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Verdel B M, Souverein P C, Egberts A C G and Leufkens H G M 2006 Ann. Pharm. 40 1040
Bonola G, Da Re P, Magistretti M J, Massarani E and Setnikar I 1968 J. Med. Chem. 11 1136
Russel H E and Alaimo R J 1972 J. Med. Chem. 15 335
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
Levin J I, Chan P S, Bailey T, Katocs A S and Venkatesan A M 1994 Bioorg. Med. Chem. Lett. 4 1141
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
Xu Z, Zhang Y, Fu H, Zhong H, Hong K and Zhu W 2011 Bioorg. Med. Chem. Lett. 21 4005
Edmondson S, Danishefsky S, Sepp-lorenzinol L and Rosen N 1999 J. Am.Chem. Soc. 121 2147
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
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
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
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
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
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
Arya K and Dandia A 2007 Lett. Org. Chem. 4 378
Sharma S D and Kaur V 1989 Synthesis 677
Qiao R Z, Xu B L and Wang Y H 2007 Chin. Chem. Lett. 18 656
Cai G P, Xu X L and Li Z F 2002 J. Heterocycl. Chem. 39 1271
Asakawa H and Matano M 1979 Chem. Pharm. Bull. 27 1287
Connolly D J, Cusack D, O’sullivan T P and Guiry P J 2005 Tetrahedron 61 10153
Su W K and Yang B B 2002 Aust. J. Chem. 55 695
Shi D Q, Rong L C and Wang J X 2004 Chem. J. Chin. Univ. 25 2051
Shi D Q, Wang J X and Rong L C 2003 J. Chem. Res. Synop. 671
Shi D Q, Rong L C and Wang J X 2003 Tetrahedron Lett. 44 3199
Shi D Q, Shi C L and Wang J X 2005 J. Heterocycl. Chem. 40 173
Shaabani A, Maleki A and Mofakham H 2008 Synth. Commun. 38 3751
Chen J X, Su W K and Wu H Y 2007 Green Chem. 9 972
Hsu H, Tseng C C, Matii B and Sun C M 2012 Mol. Divers 16 241
Rostami A, Tahmasbi B, Gholami H and Taymorian H 2013 Chin. Chem. Lett. 24 211
Mohammadi A A, Dabiri M and Qaraat H 2009 Tetrahedron 65 3804
Kefayati H, Vazifeh M and Kazemi-Rad R 2013 J. Chin. Chem. Soc. 60 1197
Narasimhulu M and Lee Y R 2011 Tetrahedron 67 9627
Hu Y, Wang M M, Chen H and Shi D Q 2011 Tetrahedron 67 9342
Bergman J, Engqvist R, Stalhandskec C and Wallbergd H 2003 Tetrahedron 59 1033
Jiang Y, Liu Y, Tu S J and Shi F 2013 Tetrahedron: Asymmetry 24 1286
Dabiri M, Mohammadi A A and Qaraat H 2009 Monatsh. Chem. 140 401
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
Varma R S 1999 Green Chem. 1 43
Heravi M M, Baghernejad B and Oskooie H A 2009 Curr. Org. Chem. 13 1002
Heravi M M, Alinejhad H and Bakhtiari K 2010 Mol. Divers. 14 621
Li J P, Qiu J K and Li H 2011 J. Chin. J. Chem. 29 511
Mane M M and Pore D M 2014 Tetrahedron Lett. 55 6601
Hegade P G, Mane M M, Patil J D and Pore D M 2014 Synth. Commun. 1 1
Mane M M and Pore D M 2015 Synth. Commun. 1 868
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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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