{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,5]],"date-time":"2026-08-05T00:34:48Z","timestamp":1785890088129,"version":"3.56.0"},"reference-count":17,"publisher":"American Chemical Society (ACS)","issue":"13","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Org. Lett."],"published-print":{"date-parts":[[2005,6,1]]},"DOI":"10.1021\/ol050614e","type":"journal-article","created":{"date-parts":[[2005,6,16]],"date-time":"2005-06-16T04:49:55Z","timestamp":1118897395000},"page":"2567-2569","source":"Crossref","is-referenced-by-count":22,"title":["Facile Conversion of <i>o<\/i>-Quinones into 1,3-Dioxoles"],"prefix":"10.1021","volume":"7","author":[{"given":"Belen","family":"Batanero","sequence":"first","affiliation":[{"name":"Department of Organic Chemistry, University of Alcal\u00e1, 28871 Alcal\u00e1 de Henares, Madrid, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fructuoso","family":"Barba","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry, University of Alcal\u00e1, 28871 Alcal\u00e1 de Henares, Madrid, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2005,5,21]]},"reference":[{"key":"ol050614eb00001\/ol050614eb00001_1","first-page":"781","volume-title":"Comprehensive Heterocyclic Chemistry","volume":"6","author":"Elliott A.","year":"1984"},{"key":"ol050614eb00002\/ol050614eb00002_1","doi-asserted-by":"crossref","first-page":"157","DOI":"10.1016\/S0223-5234(00)00106-9","volume":"35","author":"Vanelle P.","year":"2000","journal-title":"Eur. J. Med. Chem."},{"key":"ol050614eb00003\/ol050614eb00003_1","doi-asserted-by":"crossref","first-page":"14994","DOI":"10.1021\/bi048801s","volume":"43","author":"Kwon K.","year":"2004","journal-title":"Biochemistry"},{"key":"ol050614eb00004\/ol050614eb00004_1","doi-asserted-by":"crossref","unstructured":"Grosset, V.; Danvy, D.; Capet, M.Tetrahedron:\u2009 Asymmetry2003,14, 2335.","DOI":"10.1016\/S0957-4166(03)00458-0"},{"key":"ol050614eb00005\/ol050614eb00005_1","doi-asserted-by":"crossref","first-page":"3607","DOI":"10.1016\/j.bmcl.2004.03.084","volume":"14","author":"Baraldi P. G.","year":"2004","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ol050614eb00006\/ol050614eb00006_1","doi-asserted-by":"crossref","first-page":"471","DOI":"10.1097\/00005344-200104000-00014","volume":"37","author":"Iwasaki T.","year":"2001","journal-title":"J. Cardiovasc. Pharm."},{"key":"ol050614eb00007\/ol050614eb00007_1","doi-asserted-by":"crossref","first-page":"4533","DOI":"10.1016\/j.bmcl.2004.06.035","volume":"14","author":"Wu Y. J.","year":"2004","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ol050614eb00008\/ol050614eb00008_1","first-page":"563","volume-title":"Comprehensive Heterocyclic Chemistry","volume":"3","author":"Elliott A.","year":"1996"},{"key":"ol050614eb00009\/ol050614eb00009_1","doi-asserted-by":"crossref","first-page":"3504","DOI":"10.1021\/ja01477a035","volume":"83","author":"Field N. D.","year":"1961","journal-title":"J. Am. Chem. Soc."},{"key":"ol050614eb00010\/ol050614eb00010_1","doi-asserted-by":"crossref","first-page":"93","DOI":"10.3987\/COM-88-S38","volume":"28","author":"Jung M. E.","year":"1989","journal-title":"Heterocycles"},{"key":"ol050614eb00011\/ol050614eb00011_1","doi-asserted-by":"crossref","first-page":"6551","DOI":"10.1021\/ja00773a060","volume":"94","author":"Sheehan J.","year":"1972","journal-title":"J. Am. Chem. Soc."},{"key":"ol050614eb00012\/ol050614eb00012_1","doi-asserted-by":"crossref","first-page":"4181","DOI":"10.1016\/S0040-4039(01)82098-0","volume":"22","author":"Alonso M.","year":"1981","journal-title":"Tetrahedron Lett."},{"key":"ol050614eb00013\/ol050614eb00013_1","first-page":"3447","volume":"50","author":"Alonso M.","year":"1985","journal-title":"J. Org. Chem."},{"key":"ol050614eb00014\/ol050614eb00014_1","doi-asserted-by":"crossref","first-page":"817","DOI":"10.1055\/s-2000-6271","author":"Nakashima H.","year":"2000","journal-title":"Synthesis"},{"key":"ol050614eb00015\/ol050614eb00015_1","doi-asserted-by":"crossref","first-page":"133","DOI":"10.1016\/0022-0728(95)04402-7","volume":"405","author":"Compounds","year":"1996","journal-title":"J. Electroanal. Chem."},{"key":"ol050614eb00016\/ol050614eb00016_1","doi-asserted-by":"crossref","first-page":"8901","DOI":"10.1021\/ja00206a020","volume":"111","author":"Carter M. T.","year":"1989","journal-title":"J. Am. Chem. Soc."},{"key":"ol050614eb00017\/ol050614eb00017_1","unstructured":"Phenanthrene[9,10-d]1,3-dioxole (2a)(817 mg, 92% yield). Mp 120\u2212121 \u00b0C. IR (KBr) \u03bd = 3063, 2906, 1658, 1609, 1520, 1450, 1372, 1118, 1073, 751, 720 cm-1.1H NMR (300 MHz, CDCl3) \u03b4:\u2009 6.27(s, 2H), 7.57(t, 2H,J= 7 Hz), 7.64(t, 2H,J= 7 Hz), 7.94(d, 2H,J= 7.8 Hz), 8.66(d, 2H,J= 7.8 Hz).13C NMR (75.4 MHz, CDCl3) \u03b4:\u2009 101.77, 120.0, 121.2, 123.3, 124.7, 126.9, 127.3, 137.8. MSm\/e(relative intensity) EI:\u2009 223(M++ 1, 16), 222(M+, 100), 194(11), 180(11), 163(45), 152(6), 111(12), 82(15), 63(8). Anal. Calcd for C15H10O2:\u2009 C, 81.08; H, 4.50. Found:\u2009 C, 81.27; H, 4.39.1,10-Phenanthroline[5,6-d]1,3-dioxole (2b)(1098 mg, 98% yield). Mp 240\u2212242\u00b0C. IR (KBr) \u03bd = 3058, 2921, 1661, 1590, 1517, 1459, 1364, 1067, 1027, 794, 734 cm-1.1H NMR (300 MHz, CDCl3) \u03b4:\u2009 6.32(s, 2H), 7.61(dd, 2H,J1= 8.1 Hz,J2= 4.4 Hz), 8.25(dd, 2H,J1= 8.1 Hz,J2= 1.8 Hz), 9.07(dd, 2H,J1= 4.4 Hz,J2= 1.8 Hz).13C NMR (75.4 MHz, CDCl3) \u03b4:\u2009 103, 118.2, 123.2, 128.3, 137.4, 142.8, 148.5. MSm\/e(relative intensity) EI:\u2009 225(M++ 1, 15), 224(M+, 100), 196(6), 166(32), 139(20), 112(14), 88(5). Anal. Calcd for C13H8N2O2:\u2009 C, 69.64; H, 3.57; N, 12.50. Found:\u2009 C, 69.39; H, 3.33; N, 12.71.Naphtho[1,2-d]1,3-dioxole (2c)(320 mg, 37% yield). Mp 84\u221287\u00b0C. IR (KBr) \u03bd = 3058, 2887, 1650, 1604, 1466, 1413, 1281, 1060, 799 cm-1.1H NMR (300 MHz, CDCl3) \u03b4:\u2009 6.16(s, 2H), 7.2(d, 1H,J= 8.6 Hz), 7.29\u22127.36(m, 1H), 7.4\u22127.48(m, 2H), 7.8(t, 2H,J= 7.4 Hz).13C NMR (75.4 MHz, CDCl3) \u03b4:\u2009 101.8, 110.6, 119.8, 121.9, 124.1, 126.4, 128.6, 130.2, 141.3, 143.4. MSm\/e(relative intensity) EI:\u2009 173(M++ 1, 12), 172(M+, 100), 171(M+\u2212 1, 72), 130(11), 114(55), 86(21), 74(11), 63(23), 51(12). Anal. Calcd for C11H8O2:\u2009 C, 76.74; H, 4.65. Found:\u2009 C, 76.61; H, 4.82.4-Sulfonicacid tetraethylammonium salt-naphtho[1,2-d]1,3-dioxole (2d)(1657 mg, 87% yield). Mp 144\u2212146\u00b0C. IR (KBr) \u03bd = 3050, 2987, 1644, 1605, 1461, 1326, 1204, 1022, 763, 733, 630 cm-1.1H NMR (300 MHz, CDCl3) \u03b4:\u2009 0.82(t, 12H,J= 7 Hz), 2.77(c, 8H,J= 7 Hz), 6.0(s, 2H), 7.15\u22127.35(m, 2H), 7.62(d, 1H,J= 8 Hz), 7.77(s, 1H), 8.72(d, 1H,J= 7.7 Hz).13C NMR (75.4 MHz, CDCl3) \u03b4:\u2009 7.2, 52.0, 102.0, 110.8, 119.6, 119.8, 124.7, 126.1, 127.8, 137.2, 141.3, 142.3. MSm\/e(relative intensity) ESI(\u2212):\u2009 252(M++ 1, 8), 251(M+, 100). ESI(+):\u2009 131(M++ 1, 11), 130(M+, 100). Anal. Calcd for C19H27NO5S:\u2009 C, 59.84; H, 7.09; N, 3.67. Found:\u2009 C, 60.10; H, 6.92; N, 3.72.5,6-Dimethoxy-benzo[1,3]dioxole (2e)(164 mg, 18% yield). Mp 77\u221279\u00b0C. IR (KBr) \u03bd = 3003, 2925, 1509, 1466, 1215, 1184, 1165, 1031, 925, 813 cm-1.1H NMR (300 MHz, CDCl3) \u03b4:\u2009 3.82(s, 6H), 5.88(s, 2H), 6.58(s, 2H).13C NMR (75.4 MHz, CDCl3) \u03b4:\u2009 57.3, 96.4, 101.2, 125.7, 140.9. MSm\/e(relative intensity) EI:\u2009 183(M++ 1, 10), 182(M+, 100), 167(63), 121(18), 109(76), 81(49), 69(56), 53(77). Anal. Calcd for C9H10O4:\u2009 C, 59.34; H, 6.59. Found:\u2009 C, 59.60; H, 6.68."}],"container-title":["Organic Letters"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/ol050614e","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2021,10,17]],"date-time":"2021-10-17T04:48:41Z","timestamp":1634446121000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/ol050614e"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2005,5,21]]},"references-count":17,"journal-issue":{"issue":"13","published-print":{"date-parts":[[2005,6,1]]}},"alternative-id":["10.1021\/ol050614e"],"URL":"https:\/\/doi.org\/10.1021\/ol050614e","relation":{},"ISSN":["1523-7060","1523-7052"],"issn-type":[{"value":"1523-7060","type":"print"},{"value":"1523-7052","type":"electronic"}],"subject":[],"published":{"date-parts":[[2005,5,21]]}}}