{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,17]],"date-time":"2026-08-17T14:30:30Z","timestamp":1786977030494,"version":"build-2736575974"},"reference-count":79,"publisher":"Wiley","issue":"23","license":[{"start":{"date-parts":[[2022,10,21]],"date-time":"2022-10-21T00:00:00Z","timestamp":1666310400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["aces.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry \u0097 An Asian Journal"],"published-print":{"date-parts":[[2022,12]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>A catalyst\u2010, metal\u2010 and base\u2010free unprecedented one\u2010pot multicomponent synthetic strategy has been established for the construction of various substituted morpholine glycoconjugates through four\u2010component reactions of glycosyl amino alcohol, chloroacetone, acid, and isocyanides. Unexpectedly, this one\u2010pot approach generates only the cyclized morpholine scaffolds rather than normal Ugi adduct without any external base. This reaction proceeds via in\u2005situ formations of Schiff\u2010base followed by an intramolecular halogen displacement process, finally the Joullie\u2010Ugi reaction takes place leading to the corresponding products with a mixture of diastereomers.<\/jats:p>","DOI":"10.1002\/asia.202200849","type":"journal-article","created":{"date-parts":[[2022,9,28]],"date-time":"2022-09-28T13:34:28Z","timestamp":1664372068000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["Catalyst\u2010 and Base\u2010free One\u2010pot, Multicomponent, De Novo Assembly of Structurally Diverse Morpholine Glycoconjugates"],"prefix":"10.1002","volume":"17","author":[{"given":"Ariza","family":"Khanam","sequence":"first","affiliation":[{"name":"Medicinal and Process Chemistry Division CSIR-Central Drug Research Institute, BS-10\/1, Sector 10, Jankipuram Extension  Sitapur Road, P.O. Box 173 Lucknow 226 031 India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mohan","family":"Lal","sequence":"additional","affiliation":[{"name":"Medicinal and Process Chemistry Division CSIR-Central Drug Research Institute, BS-10\/1, Sector 10, Jankipuram Extension  Sitapur Road, P.O. Box 173 Lucknow 226 031 India"},{"name":"Chemical Science Academy of Scientific and Innovative Research (AcSIR)  Ghaziabad 201002 India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5813-9756","authenticated-orcid":false,"given":"Pintu Kumar","family":"Mandal","sequence":"additional","affiliation":[{"name":"Medicinal and Process Chemistry Division CSIR-Central Drug Research Institute, BS-10\/1, Sector 10, Jankipuram Extension  Sitapur Road, P.O. Box 173 Lucknow 226 031 India"},{"name":"Chemical Science Academy of Scientific and Innovative Research (AcSIR)  Ghaziabad 201002 India"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2022,10,21]]},"reference":[{"key":"e_1_2_8_1_1","unstructured":"\u00a0"},{"key":"e_1_2_8_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/med.21634"},{"key":"e_1_2_8_3_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2020.103578"},{"key":"e_1_2_8_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/cmdc.201900682"},{"key":"e_1_2_8_5_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200900744"},{"key":"e_1_2_8_6_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2018.08.040"},{"key":"e_1_2_8_7_1","unstructured":"\u00a0"},{"key":"e_1_2_8_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm501100b"},{"key":"e_1_2_8_9_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2019.02.015"},{"key":"e_1_2_8_10_1","first-page":"281","volume":"7","author":"Al-Ghorbani M.","year":"2015","journal-title":"J. Chem Pharm Res."},{"key":"e_1_2_8_11_1","first-page":"40","volume":"3","author":"Naim M. J.","year":"2015","journal-title":"Int. J. Pharm. Pharm. Sci."},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2019.02.015"},{"key":"e_1_2_8_13_1","unstructured":"\u00a0"},{"key":"e_1_2_8_14_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1527-3458.2003.tb00245.x"},{"key":"e_1_2_8_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm980299k"},{"key":"e_1_2_8_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm950654w"},{"key":"e_1_2_8_17_1","first-page":"1777","volume":"14","author":"Kumar R.","year":"2016","journal-title":"Int. J. Chem. Sci."},{"key":"e_1_2_8_18_1","unstructured":"\u00a0"},{"key":"e_1_2_8_19_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-2004-816003"},{"key":"e_1_2_8_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm501100b"},{"key":"e_1_2_8_21_2","doi-asserted-by":"publisher","DOI":"10.1134\/S1070428013060018"},{"key":"e_1_2_8_22_1","unstructured":"For examples of intramolecular cyclization strategies see:"},{"key":"e_1_2_8_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo9007223"},{"key":"e_1_2_8_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.6b03807"},{"key":"e_1_2_8_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol301203z"},{"key":"e_1_2_8_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja104168q"},{"key":"e_1_2_8_27_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2015.12.015"},{"key":"e_1_2_8_28_1","unstructured":"For other selected examples of metal-catalyzed morpholine synthesis by C\u2212N bond formation see:"},{"key":"e_1_2_8_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol202276h"},{"key":"e_1_2_8_30_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201206826"},{"key":"e_1_2_8_30_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201206826"},{"key":"e_1_2_8_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo100408p"},{"key":"e_1_2_8_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.6b02260"},{"key":"e_1_2_8_33_1","unstructured":"For other selected examples of metal-catalyzed morpholine synthesis by C\u2212O bond formation see:"},{"key":"e_1_2_8_34_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00070a001"},{"key":"e_1_2_8_35_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5QO00060B"},{"key":"e_1_2_8_36_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.1c02539"},{"key":"e_1_2_8_37_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201002606"},{"key":"e_1_2_8_38_1","unstructured":"\u00a0"},{"key":"e_1_2_8_39_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja511232b"},{"key":"e_1_2_8_40_2","first-page":"43","volume":"48","author":"Luescher M. U.","year":"2015","journal-title":"Aldrichimica Acta"},{"key":"e_1_2_8_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo5001252"},{"key":"e_1_2_8_42_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201505167"},{"key":"e_1_2_8_42_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201505167"},{"key":"e_1_2_8_43_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.6b00722"},{"key":"e_1_2_8_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b00611"},{"key":"e_1_2_8_45_1","unstructured":"\u00a0"},{"key":"e_1_2_8_46_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200800373"},{"key":"e_1_2_8_46_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200800373"},{"key":"e_1_2_8_47_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.5b02516"},{"key":"e_1_2_8_48_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c06632"},{"key":"e_1_2_8_49_1","unstructured":"\u00a0"},{"key":"e_1_2_8_50_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b03141"},{"key":"e_1_2_8_51_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201712350"},{"key":"e_1_2_8_51_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201712350"},{"key":"e_1_2_8_52_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6OB02284G"},{"key":"e_1_2_8_53_1","unstructured":"\u00a0"},{"key":"e_1_2_8_54_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr100233r"},{"key":"e_1_2_8_55_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr0505728"},{"key":"e_1_2_8_56_2","doi-asserted-by":"publisher","DOI":"10.2174\/0929867023368719"},{"key":"e_1_2_8_57_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO;2-U"},{"key":"e_1_2_8_58_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b00862"},{"key":"e_1_2_8_59_1","unstructured":"\u00a0"},{"key":"e_1_2_8_60_2","doi-asserted-by":"publisher","DOI":"10.2174\/138955712803832654"},{"key":"e_1_2_8_61_2","doi-asserted-by":"publisher","DOI":"10.2174\/138955711793564060"},{"key":"e_1_2_8_62_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm900819p"},{"key":"e_1_2_8_63_1","unstructured":"\u00a0"},{"key":"e_1_2_8_64_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo200260w"},{"key":"e_1_2_8_65_2","unstructured":"B.Whittaker C.Steele D.Hardick M.Dale V.Pomel A.Quattropani D.Beher Eur. Pat. Appl. EP 2687528A1 20140122 2014."},{"key":"e_1_2_8_66_1","doi-asserted-by":"publisher","DOI":"10.1038\/nprot.2007.71"},{"key":"e_1_2_8_67_1","unstructured":"For details see the Supporting Information."},{"key":"e_1_2_8_68_1","unstructured":"\u00a0"},{"key":"e_1_2_8_69_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.0c02103"},{"key":"e_1_2_8_70_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(97)00607-2"},{"key":"e_1_2_8_71_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00385a080"},{"key":"e_1_2_8_72_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.6b00827"},{"key":"e_1_2_8_73_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201001592"},{"key":"e_1_2_8_74_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscombsci.0c00046"},{"key":"e_1_2_8_75_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsomega.9b03684"}],"container-title":["Chemistry \u2013 An Asian Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/asia.202200849","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/asia.202200849","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/aces.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/asia.202200849","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,8]],"date-time":"2025-10-08T15:27:13Z","timestamp":1759937233000},"score":1,"resource":{"primary":{"URL":"https:\/\/aces.onlinelibrary.wiley.com\/doi\/10.1002\/asia.202200849"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,10,21]]},"references-count":79,"journal-issue":{"issue":"23","published-print":{"date-parts":[[2022,12]]}},"alternative-id":["10.1002\/asia.202200849"],"URL":"https:\/\/doi.org\/10.1002\/asia.202200849","archive":["Portico"],"relation":{},"ISSN":["1861-4728","1861-471X"],"issn-type":[{"value":"1861-4728","type":"print"},{"value":"1861-471X","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,10,21]]},"assertion":[{"value":"2022-08-16","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2022-10-21","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202200849"}}