{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,4]],"date-time":"2026-04-04T07:12:31Z","timestamp":1775286751422,"version":"3.50.1"},"reference-count":27,"publisher":"Elsevier BV","issue":"31","license":[{"start":{"date-parts":[[2003,7,1]],"date-time":"2003-07-01T00:00:00Z","timestamp":1057017600000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/tdm\/userlicense\/1.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Tetrahedron Letters"],"published-print":{"date-parts":[[2003,7]]},"DOI":"10.1016\/s0040-4039(03)01374-1","type":"journal-article","created":{"date-parts":[[2003,7,16]],"date-time":"2003-07-16T17:58:06Z","timestamp":1058378286000},"page":"5893-5896","source":"Crossref","is-referenced-by-count":26,"title":["One-pot synthesis of 2-(2-hydroxyaryl)quinolines: reductive coupling reactions of 2\u2032-hydroxy-2-nitrochalcones"],"prefix":"10.1016","volume":"44","author":[{"given":"Ana I.R.N.A","family":"Barros","sequence":"first","affiliation":[]},{"given":"Artur M.S","family":"Silva","sequence":"additional","affiliation":[]}],"member":"78","reference":[{"key":"10.1016\/S0040-4039(03)01374-1_BIB1","first-page":"245","volume":"5","author":"Balasubramanian","year":"1996"},{"key":"10.1016\/S0040-4039(03)01374-1_BIB2","first-page":"167","volume":"5","author":"Jones","year":"1996"},{"key":"10.1016\/S0040-4039(03)01374-1_BIB4","doi-asserted-by":"crossref","first-page":"85","DOI":"10.1039\/a605294k","author":"Meth-Cohn","year":"1997","journal-title":"J. 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Abstr. 1990, 112, 235197g."},{"key":"10.1016\/S0040-4039(03)01374-1_BIB22","doi-asserted-by":"crossref","first-page":"569","DOI":"10.1016\/S0040-4039(00)74829-5","volume":"32","author":"Larock","year":"1991","journal-title":"Tetrahedron Lett."},{"key":"10.1016\/S0040-4039(03)01374-1_BIB23","doi-asserted-by":"crossref","first-page":"1625","DOI":"10.1016\/0040-4039(93)85025-R","volume":"34","author":"Kundu","year":"1993","journal-title":"Tetrahedron Lett."},{"key":"10.1016\/S0040-4039(03)01374-1_BIB24","doi-asserted-by":"crossref","first-page":"37","DOI":"10.1016\/1381-1169(96)00123-9","volume":"111","author":"Cenini","year":"1996","journal-title":"J. Mol. Catal. A: Chem."},{"key":"10.1016\/S0040-4039(03)01374-1_BIB25","doi-asserted-by":"crossref","first-page":"108","DOI":"10.3184\/030823401103169153","author":"Ma","year":"2001","journal-title":"J. Chem. Res."},{"key":"10.1016\/S0040-4039(03)01374-1_BIB26","doi-asserted-by":"crossref","first-page":"641","DOI":"10.1039\/a902554e","volume":"23","author":"Boix","year":"1999","journal-title":"New J. Chem."},{"key":"10.1016\/S0040-4039(03)01374-1_BIB27","unstructured":"Typical procedure with SnCl2\u00b72H2O in HCl\/AcOH: A solution of hydrated stannous chloride (5.2 g, 23 mmol) in concentrated hydrochloric acid (20 mL) was added to a suspension of the appropriate 2\u2032-hydroxy-2-nitrochalcone 1a\u2013d (5.7 mmol) in acetic acid (60 mL). The mixture was heated at 90\u00b0C for 4 h. After that period, the solution was cooled and treated with an excess of a 25% aqueous sodium hydroxide solution. The residue obtained was extracted with chloroform (2\u00d750 mL) dried over Na2SO4 and evaporated to dryness. In the case of 4\u2032-substituted-2\u2032-hydroxy-2-nitrochalcones 1c,d, the residue was purified by silica gel column chromatography, using chloroform as eluent, giving after evaporation and recrystallisation from ethanol 2-(2-hydroxyaryl)quinolines 3c,d (3c, 66%; 3d, 58%). For 2\u2032-hydroxy-2-nitrochalcones 1a,b, the obtained residue was purified by silica gel column chromatography, using as eluent 1:3 and 1:1 mixtures of chloroform-light petroleum to respectively collect 2-(2-hydroxyaryl)quinolines 3a,b and 2-(2-hydroxyaryl)quinoline-N-oxides 2a\u2013b (2a, 47%; 3a, 23%; 2b, 44%; 3b, 27%)."},{"key":"10.1016\/S0040-4039(03)01374-1_BIB29","doi-asserted-by":"crossref","first-page":"1655","DOI":"10.1080\/00387019708006750","volume":"30","author":"Silva","year":"1997","journal-title":"Spectrosc. 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Chem."},{"key":"10.1016\/S0040-4039(03)01374-1_BIB32","unstructured":"Spectroscopic data for 2-(2-hydroxyphenyl)quinoline 3a: mp: 109.8\u2013110.7\u00b0C; 1H NMR (300.13 MHz, DMSO-d6): \u03b4 6.97\u20137.03 (m, 2H, H-3\u2032 and H-5\u2032), 7.41 (dt, 1H, H-4\u2032, J=1.2 and 7.7 Hz), 7.67 (dt, 1H, H-6, J=0.7 and 7.7 Hz), 7.85 (dt, 1H, H-7, J=1.1 and 7.7 Hz), 8.05\u20138.10 (m, 2H, H-5 and H-8), 8.22 (dd, 1H, H-6\u2032, J=1.2 and 7.7 Hz), 8.39 (d, 1H, H-3, J=8.9 Hz), 8.59 (d, 1H, H-4, J=8.9 Hz), 14.93 (s, 1H, OH); 13C NMR (75.47 MHz, DMSO-d6): \u03b4 118.0 (C-3 and C-3\u2032), 118.8 (C-1\u2032), 118.9 (C-5\u2032), 126.4 (C-4a), 127.0 (C-6 and C-8), 127.9 (C-6\u2032), 128.0 (C-5), 130.9 (C-7), 132.2 (C-4\u2032), 138.4 (C-4), 144.1 (C-8a), 157.7 (C-2), 160.2 (C-2\u2032); EI-MS: m\/z (rel. intensity) 221 (M+, 100), 220 (59), 193 (25), 180 (15), 167 (30), 154 (7), 128 (16), 111 (8), 96 (10), 89 (4), 84 (15), 77 (9), 63 (7). Anal. calcd for C15H11NO: C, 81.45; H, 4.98; N, 6.33. Found: C, 81.40; H, 5.02; N, 6.30%."},{"key":"10.1016\/S0040-4039(03)01374-1_BIB34","first-page":"184","volume":"2","author":"Roberts","year":"1979"}],"container-title":["Tetrahedron Letters"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0040403903013741?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0040403903013741?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2021,6,8]],"date-time":"2021-06-08T17:51:47Z","timestamp":1623174707000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S0040403903013741"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2003,7]]},"references-count":27,"journal-issue":{"issue":"31","published-print":{"date-parts":[[2003,7]]}},"alternative-id":["S0040403903013741"],"URL":"https:\/\/doi.org\/10.1016\/s0040-4039(03)01374-1","relation":{},"ISSN":["0040-4039"],"issn-type":[{"value":"0040-4039","type":"print"}],"subject":[],"published":{"date-parts":[[2003,7]]}}}