{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,5,14]],"date-time":"2025-05-14T07:23:08Z","timestamp":1747207388448,"version":"3.40.5"},"reference-count":26,"publisher":"Bentham Science Publishers Ltd.","issue":"2","content-domain":{"domain":["eurekaselect.com"],"crossmark-restriction":true},"short-container-title":["COS"],"published-print":{"date-parts":[[2020,5,8]]},"abstract":"<jats:sec>\n<jats:title>Objective:<\/jats:title>\n<jats:p>To develop efficient method for the synthesis of naphtha-quinoxaline derivatives via the\nreaction of \u03b2-lapachone with various 1,2-diamines.<\/jats:p>\n<\/jats:sec>\n<jats:sec>\n<jats:title>Methods:<\/jats:title>\n<jats:p>A mixture of \u03b2-lapachone (1mmol), 1,2-diamine (1mmol) and graphene oxide (20mg) in methanol\n(3mL) was heated at 60\u00b0C, under constant stirring for appropriate time. After completion of the reaction, the\ncatalyst was filtered off, washed with ethyl acetate (3x3mL) and the combined filtrate was washed with H2O,\ndried (anhy. Na2SO4) and concentrated under vacuum. The residue was chromatographed over a column of\nsilica gel eluting with a mixture of hexane and ethyl acetate in different ratios, to afford the desired product. All\nsynthesized compounds were assigned with the help of analytical and 1H, 13C NMR, IR, and mass spectral\nstudies.<\/jats:p>\n<\/jats:sec>\n<jats:sec>\n<jats:title>Results:<\/jats:title>\n<jats:p>To establish the catalytic role of GO in the synthesis of naphtha-quinoxaline derivatives, the reaction\nof \u03b2-lapachone with 3,4-diaminotoluene was selected as a model reaction. The catalytic activity of graphene\noxide in comparison with other catalysts like acidic resin amberlyst-15 and solid acid catalyst like\nmontmorillonite K-10 were studied. The reaction was also observed in various solvents such as water,\nacetonitrile, toluene, dichloromethane, ethanol and 1,4-dioxane using GO as a catalyst. Excellent yields were\nobtained at 60\u00b0C in methanol. The efficacy of the present protocol was investigated by the reaction of \u03b2-\nlapachone with other 1,2-diamines.<\/jats:p>\n<\/jats:sec>\n<jats:sec>\n<jats:title>Conclusion:<\/jats:title>\n<jats:p>An attractive green metal free carbocatalyst Graphene Oxide (GO) has been successfully utilized\nfor the expedient synthesis of naphtha-quinoxaline derivatives. GO showed high catalytic activity which is\nattested by the desired products being produced in shorter time. The main advantage of this method is the\nreusability of the catalyst which makes the procedure sustainable.<\/jats:p>\n<\/jats:sec>","DOI":"10.2174\/1570179416666191210102358","type":"journal-article","created":{"date-parts":[[2019,12,10]],"date-time":"2019-12-10T13:10:46Z","timestamp":1575983446000},"page":"91-97","update-policy":"https:\/\/doi.org\/10.2174\/bsp_crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Facile Synthesis of Naphtha-quinoxaline Derivatives from \u03b2-lapachone Using Graphene Oxide as Catalyst"],"prefix":"10.2174","volume":"17","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-3654-2373","authenticated-orcid":true,"given":"Pooja","family":"Vyas","sequence":"first","affiliation":[{"name":"Department of Chemistry, Mohanlal Sukhadia University, Udaipur-313001, India"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2932-5963","authenticated-orcid":true,"given":"Barkha Darra","family":"Wadhwani","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Mohanlal Sukhadia University, Udaipur-313001, India"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3983-4363","authenticated-orcid":true,"given":"Ravindra Singh","family":"Rao","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Mohanlal Sukhadia University, Udaipur-313001, India"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2443-4041","authenticated-orcid":true,"given":"Poonam","family":"Khandelwal","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Mohanlal Sukhadia University, Udaipur-313001, India"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"965","reference":[{"key":"ref=1","first-page":"3712","volume":"55","author":"Li C.J.","year":"1995","unstructured":"Li C.J.; Wang C.; Pardee A.B.; Induction of apoptosis by \u03b2-lapachone in human prostate cancer cells. Cancer Res 1995,55(17),3712-3715","journal-title":"Cancer Res"},{"key":"ref=2","doi-asserted-by":"publisher","first-page":"437","DOI":"10.1097\/00001813-199806000-00011","volume":"9","author":"Dolan M.E.","year":"1998","unstructured":"Dolan M.E.; Frydman B.; Thompson C.B.; Diamond A.M.; Garbiras B.J.; Safa A.R.; Beck W.T.; Marton L.J.; Effects of 1,2-naphthoquinones on human tumor cell growth and lack of cross-resistance with other anticancer agents. Anticancer Drugs Available at1998,9(5),437-448","journal-title":"Anticancer Drugs"},{"key":"ref=3","doi-asserted-by":"publisher","first-page":"144","DOI":"10.1006\/excr.1999.4790","volume":"255","author":"Pink J.J.","year":"2000","unstructured":"Pink J.J.; Wuerzberger-Davis S.; Tagliarino C.; Planchon S.M.; Yang X.; Froelich C.J.; Boothman D.A.; Activation of a cysteine protease in MCF-7 and T47D breast cancer cells during beta-lapachone-mediated apoptosis. Exp Cell Res Available at2000,255(2),144-155","journal-title":"Exp Cell Res"},{"key":"ref=4","first-page":"1017","volume":"26","author":"Woo H.J.","year":"2005","unstructured":"Woo H.J.; Choi Y.H.; Growth inhibition of A549 human lung carcinoma cells by beta-lapachone through induction of apoptosis and inhibition of telomerase activity. Int J Oncol 2005,26(4),1017-1023","journal-title":"Int J Oncol"},{"key":"ref=5","doi-asserted-by":"publisher","DOI":"10.1080\/14786419.2018.1440217","author":"Vyas P.","year":"2018","unstructured":"Vyas P.; Yadav D.K.; Khandelwal. P. Tectona grandis (teak) - A review on\nits phytochemical and therapeutic potential. Nat Prod Res [Formerly\nNatural Product Letters]. Available at2018","journal-title":"Nat Prod Res"},{"key":"ref=6","first-page":"1865","volume":"47B","author":"Singh P.","year":"2008","unstructured":"Singh P.; Khandelwal P.; Hara N.; Asai T.; Fujimoto Y.; Radermachol and naphthoquinone derivatives from Tecomella undulata: Complete 1H and 13C NMR assignments of radermachol with the aid of computational 13C shift prediction. Indian J Chem 2008,47B,1865-1870","journal-title":"Indian J Chem"},{"key":"ref=7","doi-asserted-by":"publisher","first-page":"303","DOI":"10.1016\/S1572-5995(05)80036-5","volume":"30","author":"Martinez M.J.A.","year":"2005","unstructured":"Martinez M.J.A.; Benito P.B.; Biological activity of quinones. Studies in Natural Products Chemistry Available at2005,30,303-366","journal-title":"Studies in Natural Products Chemistry"},{"key":"ref=8","doi-asserted-by":"publisher","first-page":"483","DOI":"10.1016\/S0968-0896(02)00542-4","volume":"11","author":"Sacau E.P.","year":"2003","unstructured":"Sacau E.P.; Est\u00e9vez-Braun A.; Ravelo A.G.; Ferro E.A.; Tokuda H.; Mukainaka T.; Nishino H.; Inhibitory effects of lapachol derivatives on epstein-barr virus activation. Bioorg Med Chem Available at2003,11(4),483-488","journal-title":"Bioorg Med Chem"},{"key":"ref=9","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1016\/0009-2797(91)90029-7","volume":"80","author":"O\u2019Brien P.J.","year":"1991","unstructured":"O\u2019Brien P.J.; Molecular mechanisms of quinone cytotoxicity. Chem Biol Interact Available at1991,80(1),1-41","journal-title":"Chem Biol Interact"},{"key":"ref=10","doi-asserted-by":"publisher","first-page":"239","DOI":"10.1016\/0378-8741(90)90061-W","volume":"29","author":"de Almeida E.R.","year":"1990","unstructured":"de Almeida E.R.; da Silva Filho A.A.; dos Santos E.R.; Lopes C.A.; Antiinflammatory action of lapachol. J Ethnopharmacol Available at1990,29(2),239-241","journal-title":"J Ethnopharmacol"},{"key":"ref=11","doi-asserted-by":"publisher","first-page":"373","DOI":"10.1055\/s-2006-959504","volume":"60","author":"Guiraud P.","year":"1994","unstructured":"Guiraud P.; Steiman R.; Campos-Takaki G.M.; Seigle-Murandi F.; Simeon de Buochberg M.; Comparison of antibacterial and antifungal activities of lapachol and \u03b2-lapachone. Planta Med Available at1994,60(4),373-374","journal-title":"Planta Med"},{"key":"ref=12","doi-asserted-by":"publisher","first-page":"729","DOI":"10.1016\/S0031-9422(97)00695-X","volume":"47","author":"Ioset J.R.","year":"1998","unstructured":"Ioset J.R.; Marston A.; Gupta M.P.; Hostettmann K.; Antifungal and larvicidal meroterpenoid naphthoquinones and a naphthoxirene from the roots of Cordia linnaei. Phytochemistry Available at1998,47(5),729-734","journal-title":"Phytochemistry"},{"key":"ref=13","doi-asserted-by":"publisher","first-page":"7752","DOI":"10.1002\/anie.200901678","volume":"48","author":"Rao C.N.","year":"2009","unstructured":"Rao C.N.; Sood A.K.; Subrahmanyam K.S.; Govindaraj A.; Graphene: the new two-dimensional nanomaterial. Angew Chem Int Ed Engl Available at2009,48(42),7752-7777","journal-title":"Angew Chem Int Ed Engl"},{"key":"ref=14","doi-asserted-by":"publisher","first-page":"537","DOI":"10.1016\/j.carbon.2005.08.005","volume":"44","author":"Szabo T.","year":"2006","unstructured":"Szabo T.; Tombacz E.; Illes E.; Dekany I.; Enhanced acidity and pH\u2010dependent surface charge characterization of successfully oxidized graphite oxide. Carbon Available at2006,44,537-545","journal-title":"Carbon"},{"key":"ref=15","doi-asserted-by":"publisher","first-page":"1170","DOI":"10.1126\/science.1158180","volume":"320","author":"Li D.","year":"2008","unstructured":"Li D.; Kaner R.B.; Materials science. Graphene-based materials. Science Available at2008,320(5880),1170-1171","journal-title":"Science"},{"key":"ref=16","doi-asserted-by":"publisher","first-page":"528","DOI":"10.1002\/adsc.201000748","volume":"353","author":"Jia H.P.","year":"2011","unstructured":"Jia H.P.; Dreyer D.R.; Bielawski C.W.; Graphite oxide as an auto-tandem oxidation\u2013hydration\u2013aldol coupling catalyst. Adv Synth Catal Available at2011,353,528-532","journal-title":"Adv Synth Catal"},{"key":"ref=17","doi-asserted-by":"publisher","first-page":"1391","DOI":"10.1016\/S0960-894X(99)00193-6","volume":"9","author":"Hamdouchi C.","year":"1999","unstructured":"Hamdouchi C.; Ezquerra J.; Vega J.A.; Vaquero J.J.; Alvarez-Builla J.; Heinz B.A.; Short synthesis and anti-rhinoviral activity of imidazo[1,2-a]pyridines: the effect of acyl groups at 3-position. Bioorg Med Chem Lett Available at1999,9(10),1391-1394","journal-title":"Bioorg Med Chem Lett"},{"key":"ref=18","doi-asserted-by":"publisher","first-page":"228","DOI":"10.1039\/B917103G","volume":"39","author":"Dreyer D.R.","year":"2010","unstructured":"Dreyer D.R.; Park S.; Bielawski C.W.; Ruoff R.S.; The chemistry of graphene oxide. Chem Soc Rev Available at2010,39(1),228-240","journal-title":"Chem Soc Rev"},{"key":"ref=19","doi-asserted-by":"publisher","first-page":"6813","DOI":"10.1002\/anie.201003238","volume":"49","author":"Dreyer D.R.","year":"2010","unstructured":"Dreyer D.R.; Jia H.P.; Bielawski C.W.; Graphene oxide: a convenient carbocatalyst for facilitating oxidation and hydration reactions. Angew Chem Int Ed Engl Available at2010,49(38),6813-6816","journal-title":"Angew Chem Int Ed Engl"},{"key":"ref=20","doi-asserted-by":"publisher","first-page":"22130","DOI":"10.1039\/c3ra44712j","volume":"3","author":"Basu B.","year":"2013","unstructured":"Basu B.; Kundu S.; Sengupta D.; Graphene oxide as a carbocatalyst: The first example of a one-pot sequential dehydration\u2013hydrothiolation of secondary aryl alcohols. RSC Advances Available at2013,3,22130-22134","journal-title":"RSC Advances"},{"key":"ref=21","doi-asserted-by":"publisher","first-page":"1339","DOI":"10.1021\/ja01539a017","volume":"80","author":"Hummers W.S.","year":"1958","unstructured":"Hummers W.S.; Offeman R.E.; Preparation of Graphitic Oxide. J Am Chem Soc Available at1958,80,1339","journal-title":"J Am Chem Soc"},{"key":"ref=22","doi-asserted-by":"publisher","first-page":"4806","DOI":"10.1021\/nn1006368","volume":"4","author":"Marcano D.C.","year":"2010","unstructured":"Marcano D.C.; Kosynkin D.V.; Berlin J.M.; Sinitskii A.; Sun Z.; Slesarev A.; Alemany L.B.; Lu W.; Tour J.M.; Improved synthesis of graphene oxide. ACS Nano Available at2010,4(8),4806-4814","journal-title":"ACS Nano"},{"key":"ref=23","doi-asserted-by":"publisher","first-page":"2776","DOI":"10.1021\/cs400468h","volume":"3","author":"Santra S.","year":"2013","unstructured":"Santra S.; Hota P.K.; Bhattacharyya R.; Bera P.; Ghosh P.; Mandal S.K.; Palladium nanoparticles on graphite oxide: A recyclable catalyst for synthesis of biaryl cores. ACS Catal Available at2013,3,2776-2789","journal-title":"ACS Catal"},{"key":"ref=24","doi-asserted-by":"publisher","first-page":"8164","DOI":"10.1039\/C5RA19066E","volume":"6","author":"Dhopte K.B.","year":"2016","unstructured":"Dhopte K.B.; Zambare R.S.; Patwardhan A.V.; Nemade P.R.; Role of graphene oxide as heterogeneous acid catalyst and benign oxidant for synthesis of benzimidazoles and benzothiazoles. RSC Advances Available at2016,6,8164-8172","journal-title":"RSC Advances"},{"key":"ref=25","doi-asserted-by":"publisher","first-page":"688","DOI":"10.1080\/00397911.2017.1281420","volume":"47","author":"Khandelwal P.","year":"2017","unstructured":"Khandelwal P.; Vyas P.; Yadav D.K.; Koolwal N.; Singh P.; Synthesis of new heterocycles through the reaction of \u03b2-lapachone with 1,2-diamines using Triton X-100 surfactant as catalyst in aqueous medium. Synth Commun Available at2017,47,688-694","journal-title":"Synth Commun"},{"key":"ref=26","first-page":"427","volume":"47B","author":"Singh P.","year":"2008","unstructured":"Singh P.; Dandia A.; Khandelwal P.; Studies on novel polycyclic heterocycles: Synthesis of new naphthaquinoxaline and naphthazaquinoxaline derivatives from naturally occurring quinones. Indian J Chem 2008,47B,427-433","journal-title":"Indian J Chem"}],"container-title":["Current Organic Synthesis"],"original-title":[],"language":"en","link":[{"URL":"http:\/\/eurekaselect.com\/article\/download\/177289","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2020,6,15]],"date-time":"2020-06-15T17:29:36Z","timestamp":1592242176000},"score":1,"resource":{"primary":{"URL":"http:\/\/www.eurekaselect.com\/177289\/article"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,5,8]]},"references-count":26,"journal-issue":{"issue":"2","published-print":{"date-parts":[[2020,5,8]]}},"alternative-id":["LiveAll1"],"URL":"https:\/\/doi.org\/10.2174\/1570179416666191210102358","relation":{},"ISSN":["1570-1794"],"issn-type":[{"type":"print","value":"1570-1794"}],"subject":[],"published":{"date-parts":[[2020,5,8]]},"assertion":[{"value":"Peer Reviewed","order":0,"name":"review_status","label":"Review Status","group":{"name":"peer_review_details","label":"Peer Review Details"}},{"value":"Single blind","order":1,"name":"review_process","label":"Review Process","group":{"name":"peer_review_details","label":"Peer Review Details"}},{"value":"Checked with iThenticate","order":0,"name":"screening_status","label":"Screening Status","group":{"name":"plagiarism_screening","label":"Plagiarism Screening"}},{"value":"2019-04-13","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2019-05-29","order":1,"name":"revised","label":"Revised","group":{"name":"publication_history","label":"Publication History"}},{"value":"2019-10-31","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2020-05-08","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}