Synthesis and Photophysical Properties of 1,4-Dihydro-2H,5H-chromeno[4,3-d][1,3]oxazin-5-ones, and Derivatives Containing Tethered 1,2,3-Triazoles, from 4-Aminocoumarins

Abstract

A facile protocol for the unprecedented one-pot H₂SO₄-mediated hydroxymethylation/cyclative N,O-acetalization of 4-aminocoumarins to 1,4-dihydro-2H,5H-chromeno[4,3-d][1,3]oxazin-5-ones, in moderate to good yields, was developed and optimized. The scope and limitations of the transformation, which takes place in water or water/THF mixtures, were also studied. The nitrogen atom of the resulting tricycles was used to tether alkyl, aryl and 1,2,3-triazolylmethyl moieties, employing a two-step click chemistry approach for the latter. The photophysical properties of the heterocycles, as well as of their 1,2,3-triazole derivatives, were also examined. The N-aryl derivatives exhibited high quantum yields of fluorescence (up to Φ_f = 0.69) and very large Stokes shifts (up to 201 nm).

Key words

4-aminocoumarins - tethered triazoles - 1,3-oxazines - cyclization reaction - photophysical properties

• References

• 1a Calcio Gaudino E, Tagliapietra S, Martina K, Palmisano G, Cravotto G. RSC Adv. 2016; 6: 46394
• 1b Wu L, Wang X, Xu W, Farzaneh F, Xu R. Curr. Med. Chem. 2009; 16: 4236
• 1c Riveiro ME, De Kimpe N, Moglioni A, Vázquez R, Monczor F, Shayo C, Davio C. Curr. Med. Chem. 2010; 17: 1325
• 1d Lacy A, O’Kennedy R. Curr. Pharm. Des. 2004; 10: 3797
• 1e Horton DA, Bourne GT, Smythe ML. Chem. Rev. 2003; 103: 893
• 1f Stefanachi A, Leonetti F, Pisani L, Catto M, Carotti A. Molecules 2018; 23: 250
• 1g Kaur M, Kohli S, Sandhu S, Bansal Y, Bansal G. Anti-Cancer Agents Med. Chem. 2015; 15: 1032
• 1h Jameel E, Umar T, Kumar J, Hoda N. Chem. Biol. Drug Des. 2016; 87: 21
• 2a Mizukami S, Okada S, Kimura S, Kikuchi K. Inorg. Chem. 2009; 48: 7630
• 2b García-Beltrán O, Cassels BK, Pérez C, Mena N, Núñez MT, Martínez NP. J. Mol. Struct. 2018; 1164: 260
• 2c Pavez P, Aliaga ME. Sensors 2014; 14: 1358
• 2d He L, Yang X, Liu Y, Lin W. Anal. Methods 2016; 8: 8022
• 2e Zhou Z, Li N, Tong A. Anal. Chim. Acta 2011; 702: 81
• 3a Christie RM, Morgan KM, Islam MS. Dyes Pigm. 2008; 76: 741
• 3b Katritzky AR, Narindoshvili T. Org. Biomol. Chem. 2009; 7: 627
• 3c Lin Q, Bao C, Fan G, Cheng S, Liu H, Liu Z, Zhu L. J. Mater. Chem. 2012; 22: 6680
• 4a Saeed A, Qamar R. Chem. Heterocycl. Compd. 2016; 52: 96
• 4b Gaonkar SL. Mini-Rev. Org. Chem. 2019; 16: 43
• 5a Huang JW, Jiang SH, Tan C, Zhu D. Chin. Chem. Lett. 2004; 15: 305
• 5b Yaylayan VA, Mandeville S. J. Agric. Food Chem. 1994; 42: 1841
• 5c Schmeda-Hirschmann G, Jakupovic J. Bol. Soc. Chil. Quim. 2000; 45: 645
• 5d Karadogan B, Parsons PJ. Tetrahedron 2001; 57: 8699
• 5e Cantin A, Moya P, Castillo MA, Primo J, Miranda MA, Primo-Yufera E. Eur. J. Org. Chem. 1999; 221
• 6a Zhang M, Zhang R, Yin W, Yu X, Zhang MY, Liu P, Gu Y, Zhang W. Mol. Diversity 2016; 20: 611
• 6b Bouaziz Z, Riondel J, Mey A, Berlion M, Fillion H. Eur. J. Med. Chem. 1991; 26: 469
• 6c García JJ. S, Flores-Alamo M, Klimova EM, Apan TR, Klimova EL. J. Organomet. Chem. 2018; 867: 312
• 6d Cocuzza AJ, Chidester DR, Cordova BC, Jeffrey S, Parsons RL, Bacheler LT, Erickson-Viitanen S, Trainor GL, Ko SS. Bioorg. Med. Chem. Lett. 2001; 11: 1177
• 7a Kategaonkar AH, Sonar SS, Pokalwar RU, Shingate BB, Shingare MS. Bull. Korean Chem. Soc. 2010; 31: 1657
• 7b Verma V, Singh K, Kumar D, Klapotke TM, Stierstorfer J, Narasimhan B, Qaze AK, Hamid A, Jaglan S. Eur. J. Med. Chem. 2012; 56: 195
• 7c De Clerq E. Expert Opin. Emerging Drugs 2005; 10: 241
• 8a Coburn CA, Meinke PT, Chang W, Fandozzi CM, Graham DJ, Hu B, Huang Q, Kargman S, Kozlowski J, Liu R, McCauley JA, Nomeir AA, Soll RM, Vacca JP, Wang D, Wu H, Zhong B, Olsen DB, Ludmerer SW. ChemMedChem 2013; 8: 1930
• 8b Yayla HG, Peng F, Mangion IK, McLaughlin M, Campeau L.-C, Davies IW, DiRocco DA, Knowles RR. Chem. Sci. 2016; 7: 2066
• 9a Olianas MC, Onali P. Life Sci. 1999; 65: 2233
• 9b Böhme TM, Augelli-Szafran CE, Hussein H, Pugsley T, Serpa K, Schwarz RD. J. Med. Chem. 2002; 45: 3094
• 9c Prostota Y, Coelho PJ, Pina J, de Melo JS. Photochem. Photobiol. Sci. 2011; 10: 1346
• 9d Tomasulo M, Sortino S, White AJ, Raymo FM. J. Org. Chem. 2005; 70: 8180
• 10a Froimowicz P, Rodriguez Arza C, Ohashi S, Ishida H. J. Polym. Sci., Part A: Polym. Chem. 2016; 54: 1428
• 10b Kontogiorgis CA, Hadjipavlou-Litina DJ. J. Med. Chem. 2005; 48: 6400
• 11a Nagesam M, Raju KM, Raju MS. J. Indian Chem. Soc. 1992; 69: 592
• 11b Chavan AP. J. Chem. Res. 2006; 179
• 11c Bougan S, Hassanabadi A. J. Chem. Res. 2017; 41: 136
• 11d Vovk MV, Sukach VA, Dorokhov VI. Russ. J. Org. Chem. 2007; 43: 1186
• 12a Mondal A, Rana S, Mukhopadhyay C. Tetrahedron Lett. 2014; 55: 3498
• 12b Desai RB. J. Org. Chem. 1961; 26: 5251
• 12c Mohanty N, Patnaik KK, Rout MK. J. Indian Chem. Soc. 1968; 45: 969
• 12d Mehta RH, Sethna SS. J. Indian Chem. Soc. 1963; 40: 384
• 13a Dheer D, Singh V, Shankar R. Bioorg. Chem. 2017; 71: 30
• 13b Aneja B, Azam M, Alam S, Perwez A, Maguire R, Yadava U, Kavanagh K, Daniliuc CG, Rizvi M, Hag QM. R, Abid M. ACS Omega 2018; 3: 6912
• 13c Salunke N, Thipparaboina R, Chavan RB, Lodagekar A, Mittapalli S, Nangia A, Shastri NR. J. Pharm. Biomed. Anal. 2018; 149: 185
• 14 Shi Y, Zhou CH. Bioorg. Med. Chem. Lett. 2011; 21: 956
• 15a Kraljevic TG, Hj A, Sedic M, Pavelic SK, Stepanic V, Drenjancevic D, Talapko J, Raic-Malic S. Eur. J. Med. Chem. 2016; 124: 794
• 15b Zhang W, Li Z, Zhou M, Wu F, Hou X, Luo H, Liu H, Han X, Yan G, Ding Z, Li R. Bioorg. Med. Chem. Lett. 2014; 24: 799
• 15c Duan YC, Ma YC, Zhang E, Shi XJ, Wang MM, Ye XW, Liu HM. Eur. J. Med. Chem. 2013; 62: 11
• 15d Peterson LB, Blagg BS. J. Bioorg. Med. Chem. Lett. 2010; 20: 3957
• 15e Anand A, Naik RJ, Revankar HM, Kulkarni MV, Dixit SR, Joshi SD. Eur. J. Med. Chem. 2015; 105: 194
• 16a Scattergood PA, Sinopoli A, Elliott PI. P. Coord. Chem. Rev. 2017; 350: 136
• 16b Key JA, Koh S, Timerghazin QK, Brown A, Cairo CW. Dyes Pigm. 2009; 82: 196
• 16c Lawson CP, Dierckx A, Miannay FA, Wellner E, Wilhelmsson LM, Grøtli M. Org. Biomol. Chem. 2014; 12: 5158
• 17a Padilha G, Iglesias BA, Back DF, Kaufman TS, Silveira CC. ChemistrySelect 2017; 2: 1297
• 17b Pergomet JL, Bracca AB. J, Kaufman TS. Org. Biomol. Chem. 2017; 15: 7040
• 17c Pergomet JL, Di Liberto MG, Derita MG, Bracca AB. J, Kaufman TS. Fitoterapia 2018; 125: 98
• 17d Padilha G, Birmann PT, Domingues M, Kaufman TS, Savegnano L, Silveira CC. Tetrahedron Lett. 2017; 58: 985
• 18a Hua C.-J, Zhang K, Xin M, Ying T, Gao J.-R, Jia J.-H, Li J.-J. RSC Adv. 2016; 6: 49221
• 18b Peng S, Liu S, Zhang S, Cao S, Sun J. Org. Lett. 2015; 17: 5032
• 19a Saha M, Pradhan K, Das AR. RSC Adv. 2016; 6: 55033
• 19b Kuroki Y, Akao R, Inazumi T, Noguchi M. Tetrahedron 1994; 50: 1063
• 20a Hamama WS, Hammouda M, Afsah EM. Z. Naturforsch., B 1988; 43: 483
• 20b Marcos A, Pedregal C, Avendaño C. Tetrahedron 1995; 51: 6565
• 20c Akhrem AA, Moiseenkov AM, Veselovskii VV. Chem. Heterocycl. Compd. 1973; 9: 942
• 20d Chaaban I, Greenhill JV, Akhtar P. J. Chem. Soc., Perkin Trans. 1 1979; 1593
• 20e Hammouda M, Hamama WS, Afsah EM. Z. Naturforsch., B 1987; 42: 94
• 21a Pünkösti Z, Kele P, Herner A. J. Heterocycl. Chem. 2018; 55: 1183
• 21b Hagiwara H, Kobayashi K, Hoshi T, Suzuki T, Ando M. Tetrahedron 2001; 57: 5039
• 22a Cao H, Jiang HF, Qi CR, Yao WJ, Chen HJ. Tetrahedron Lett. 2009; 50: 1209
• 22b Dhakane VD, Gholap SS, Deshmukh UP, Chavan HV, Bandgar BP. C. R. Chim. 2014; 17: 431
• 23 Vadivelu M, Raheem AA, Sugirdha S, Bhaskar G, Karthikeyan K, Praveen C. ARKIVOC 2018; (iii): 90
• 24a Abu-Eittah RH, El-Tawil BA. H. Can. J. Chem. 1985; 63: 1173
• 24b Preat J, Jacquemin D, Wathelet V, André J.-M, Perpète EA. J. Phys. Chem. A 2006; 110: 8144
• 24c Yamaji M, Okamoto H, Goto K, Kato S.-I, Tani F, Nakamura Y. Tetrahedron Lett. 2018; 59: 1216
• 25 Molecular Probes Handbook: A Guide to Fluorescent Probes and Labeling Technologies, 11th ed. Johnson I, Michell TZ. Life Technologies; Eugene (USA): 2010
• 26a Himo F, Lovell T, Hilgraf R, Rostovtsev VV, Noodleman L, Sharpless KB, Fokin VV. J. Am. Chem. Soc. 2005; 127: 210
• 26b Xu M, Kuang C, Wang Z, Yang Q, Jiang Y. Synthesis 2011; 223
• 26c Sarode PB, Bahekar SP, Chandak HS. Synlett 2016; 27: 2681
• 26d Haldón E, Nicasio MC, Pérez PJ. Org. Biomol. Chem. 2015; 13: 9528
• 27a Bassaco MM, Fortes MO, Kaufman TS, Silveira CC. RSC Adv. 2015; 5: 21112
• 27b Maestro A, Pedrosa R, Perez-Encabo A, Perez-Rueda JJ. Eur. J. Org. Chem. 2012; 1202
• 28a Yadav N, Agarwal D, Kumar S, Dixit A, Gupta R, Awasthi S. Eur. J. Med. Chem. 2018; 145: 735
• 28b Ali AA, Chetia M, Sarma D. Tetrahedron Lett. 2016; 57: 1711
• 29 Armarego WL. F, Chai CL. L. Purification of Laboratory Chemicals, 5th ed. Butterworth-Heinemann; Oxford: 2003
• 30 Auras BL, de Lucca Meller S, da Silva MP, Neves A, Cocca LH. Z, de Boni L, Hahn da Silveira C, Iglesias BA. Appl. Organomet. Chem. 2018; 32: e4318