{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,27]],"date-time":"2025-10-27T15:53:07Z","timestamp":1761580387234,"version":"build-2065373602"},"reference-count":70,"publisher":"Wiley","issue":"11","license":[{"start":{"date-parts":[[2006,3,22]],"date-time":"2006-03-22T00:00:00Z","timestamp":1142985600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Eur J Org Chem"],"published-print":{"date-parts":[[2006,6]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Diels\u2013Alder reactions of the 2\u2032\u2010hydroxychalcones <jats:bold>1a<\/jats:bold>\u2013<jats:bold>e<\/jats:bold> with <jats:italic>ortho<\/jats:italic>\u2010benzoquinodimethane (<jats:bold>3<\/jats:bold>) yielded the 3\u2010aryl\u20101,2,3,4\u2010tetrahydro\u20102\u2010naphthyl 2\u2010hydroxyphenyl ketones <jats:bold>4a<\/jats:bold>\u2013<jats:bold>e<\/jats:bold> in good yields. The dehydrogenation of the cycloadducts <jats:bold>4a<\/jats:bold>\u2013<jats:bold>e<\/jats:bold> to 3\u2010aryl\u20102\u2010naphthyl 2\u2010hydroxyphenyl ketones <jats:bold>5a<\/jats:bold>\u2013<jats:bold>e<\/jats:bold> was studied. Good results were obtained when DDQ was used as oxidant and microwave irradiation as energy source. Several benzoxanthone derivatives were also obtained as minor products. Structures of all new compounds were established by extensive NMR studies. (\u00a9 Wiley\u2010VCH Verlag GmbH &amp; Co. KGaA, 69451 Weinheim, Germany, 2006)<\/jats:p>","DOI":"10.1002\/ejoc.200500872","type":"journal-article","created":{"date-parts":[[2006,3,22]],"date-time":"2006-03-22T07:16:42Z","timestamp":1143011802000},"page":"2558-2569","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":20,"title":["Diels\u2013Alder Reactions of 2\u2032\u2010Hydroxychalcones with <i>ortho<\/i>\u2010Benzoquino\u2010dimethane: A New Synthesis of 3\u2010Aryl\u20102\u2010naphthyl 2\u2010Hydroxyphenyl Ketones"],"prefix":"10.1002","volume":"2006","author":[{"given":"Cristela M.","family":"Brito","sequence":"first","affiliation":[]},{"given":"Diana C. G. A.","family":"Pinto","sequence":"additional","affiliation":[]},{"given":"Artur M. S.","family":"Silva","sequence":"additional","affiliation":[]},{"given":"Ana M. G.","family":"Silva","sequence":"additional","affiliation":[]},{"given":"Augusto C.","family":"Tom\u00e9","sequence":"additional","affiliation":[]},{"given":"Jos\u00e9 A. S.","family":"Cavaleiro","sequence":"additional","affiliation":[]}],"member":"311","published-online":{"date-parts":[[2006,5,11]]},"reference":[{"key":"e_1_2_5_1_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2004.04.003"},{"key":"e_1_2_5_2_2","unstructured":"\u00a0"},{"key":"e_1_2_5_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/np0000872"},{"key":"e_1_2_5_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/np000406p"},{"key":"e_1_2_5_5_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2004.02.040"},{"key":"e_1_2_5_6_2","unstructured":"\u00a0"},{"key":"e_1_2_5_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo000705j"},{"key":"e_1_2_5_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm010365"},{"key":"e_1_2_5_9_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0960-894X(02)00850-8"},{"key":"e_1_2_5_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm0305974"},{"key":"e_1_2_5_11_2","unstructured":"\u00a0"},{"key":"e_1_2_5_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/np980339n"},{"key":"e_1_2_5_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo000421z"},{"key":"e_1_2_5_14_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0960-894X(01)00798-3"},{"key":"e_1_2_5_15_2","doi-asserted-by":"publisher","DOI":"10.1016\/S1011-1344(01)00202-0"},{"key":"e_1_2_5_16_2","unstructured":"\u00a0"},{"key":"e_1_2_5_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo991130x"},{"key":"e_1_2_5_18_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0968-0896(01)00312-1"},{"key":"e_1_2_5_19_2","unstructured":"\u00a0"},{"key":"e_1_2_5_20_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0031-9422(00)00208-9"},{"key":"e_1_2_5_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/np030024u"},{"key":"e_1_2_5_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/np020546u"},{"key":"e_1_2_5_23_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0968-0896(02)00641-7"},{"key":"e_1_2_5_24_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0014-5793(03)00692-6"},{"key":"e_1_2_5_25_2","doi-asserted-by":"publisher","DOI":"10.2174\/092986705774370691"},{"key":"e_1_2_5_26_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0031-9422(01)00194-7"},{"key":"e_1_2_5_27_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0031-9422(01)00120-0"},{"key":"e_1_2_5_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00067a087"},{"key":"e_1_2_5_29_2","unstructured":"\u00a0"},{"key":"e_1_2_5_30_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0968-0896(97)00125-9"},{"key":"e_1_2_5_31_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(99)00907-7"},{"key":"e_1_2_5_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo000750r"},{"key":"e_1_2_5_33_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo000538n"},{"key":"e_1_2_5_34_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(02)00096-0"},{"key":"e_1_2_5_35_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2003.09.089"},{"key":"e_1_2_5_36_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2003.12.029"},{"key":"e_1_2_5_37_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0223-5234(02)01354-5"},{"key":"e_1_2_5_38_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.talanta.2003.08.027"},{"key":"e_1_2_5_39_2","unstructured":"\u00a0"},{"key":"e_1_2_5_40_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0731-7085(00)00365-4"},{"key":"e_1_2_5_41_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0149-2918(00)87976-X"},{"key":"e_1_2_5_42_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0223-5234(01)01273-9"},{"key":"e_1_2_5_43_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1099-0690(199901)1999:1<135::AID-EJOC135>3.0.CO;2-I"},{"key":"e_1_2_5_44_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)01131-0"},{"key":"e_1_2_5_45_2","unstructured":"\u00a0"},{"key":"e_1_2_5_46_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)00906-1"},{"key":"e_1_2_5_47_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)00905-X"},{"key":"e_1_2_5_48_2","unstructured":"A. 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EI\u2010MS:m\/z(%) = 338 (95) [M+\u00b7] 337 (86) 247 (100) 218 (16) 202 (14) 189 (18) 105 (10) 91 (12) 77 (6) 65 (7)."},{"key":"e_1_2_5_54_2","unstructured":"Selected data for xanthones7d. 1\u2010(4\u2010chlorophenyl)\u20108\u2010iodo\u20101 2\u2010dihydrobenzo[c]xanthone (7d1) (7\u2009%):1H NMR:\u03b4= 3.14 (dd J= 16.3 and 1.2 Hz 1 H H\u20102trans) 3.55 (dd J= 16.3 and 7.9 Hz 1 H H\u20102cis) 4.67 (dd J= 7.9 and 1.2 Hz 1 H H\u20101) 7.10 (s 4 H H\u20102\u2032 3\u2032 5\u2032 6\u2032) 7.13 (dd J= 7.8 and 1.5 Hz 1 H H\u20109) 7.16 (t J= 7.8 Hz 1 H H\u201010) 7.21\u20137.24 (m 1 H H\u20103) 7.44\u20137.47 (m 2 H H\u20104 5) 8.18 (dd J= 7.8 and 1.5 Hz 1 H H\u201011) 8.24\u20138.27 (m 1 H H\u20106). (4\u2010Chlorophenyl)\u201010\u2010iodo\u20101 2\u2010dihydrobenzo[c]xanthone (7d2) (6\u2009%):1H NMR:\u03b4= 3.13 (dd J= 16.2 and 1.1 Hz 1 H H\u20102trans) 3.53 (dd J= 16.2 and 7.9 Hz 1 H H\u20102cis) 4.68 (dd J= 7.9 and 1.1 Hz 1 H H\u20101) 7.09 (s 4 H H\u20102\u2032 3\u2032 5\u2032 6\u2032) 7.21\u20137.24 (m 1 H H\u20103) 7.36 (d J= 8.8 Hz 1 H H\u20108) 7.41\u20137.44 (m 2 H H\u20104 5) 7.95 (dd J= 8.8 and 2.2 Hz 1 H H\u20109) 8.01\u20138.04 (m 1 H H\u20106) 8.53 (d J= 2.2 Hz 1 H H\u201011). (4\u2010Chlorophenyl)\u20108 10\u2010diiodo\u20101 2\u2010dihydrobenzo[c]xanthone(7d3) (13\u2009%):1H NMR:\u03b4= 3.14 (br. d J= 16.3 Hz 1 H H\u20102trans) 3.54 (dd J= 16.3 and 8.0 Hz 1 H H\u20102cis) 4.65 (dd J= 8.0 and 1.2 Hz 1 H H\u20101) 7.09 (s 4 H H\u20102\u2032 3\u2032 5\u2032 6\u2032) 7.22\u20137.25 (m 1 H H\u20103) 7.44\u20137.47 (m 2 H H\u20104 5) 8.19\u20138.22 (m 1 H H\u20106) 8.39 (d J= 2.1 Hz 1 H H\u20109) 8.47 (d J= 2.1 Hz 1 H H\u201011)."},{"key":"e_1_2_5_55_2","doi-asserted-by":"publisher","DOI":"10.1002\/jhet.5570330655"},{"key":"e_1_2_5_56_2","unstructured":"L. A. 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