{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,11,4]],"date-time":"2025-11-04T16:11:30Z","timestamp":1762272690098,"version":"build-2065373602"},"reference-count":21,"publisher":"MDPI AG","issue":"5","license":[{"start":{"date-parts":[[2021,3,8]],"date-time":"2021-03-08T00:00:00Z","timestamp":1615161600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100003725","name":"National Research Foundation of Korea","doi-asserted-by":"publisher","award":["2018R1D1A1B07048631, 2016R1D1A1B03930981, 2019M3E5D5066543","2016R1A6A1A03007648"],"award-info":[{"award-number":["2018R1D1A1B07048631, 2016R1D1A1B03930981, 2019M3E5D5066543","2016R1A6A1A03007648"]}],"id":[{"id":"10.13039\/501100003725","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Studies on a one-pot synthesis of novel multisubstituted 1-alkoxyindoles 1 and their mechanistic investigations are presented. The synthesis of 1 was successfully achieved through consecutive four step reactions from substrates 2. The substrates 2, prepared through a two-step synthetic sequence, underwent three consecutive reactions of nitro reduction, intramolecular condensation, and nucleophilic 1,5-addition to provide the intermediates, 1-hydroxyindoles 8, which then were alkylated in situ with alkyl halide to afford the novel target products 1. We optimized the reaction conditions for 1 focusing on the alkylation step, along with the consideration of formation of intermediates 8. The optimized condition was SnCl2\u00b72H2O (3.3 eq) and alcohols (R1OH, 2.0 eq) for 1\u20132 h at 40 \u00b0C and then, base (10 eq) and alkyl halides (R2Y, 2.0 eq) for 1\u20134 h at 25\u201350 \u00b0C. Notably, all four step reactions were performed in one-pot to give 1 in good to modest yields. Furthermore, the mechanistic aspects were also discussed regarding the reaction pathways and the formation of side products. The significance lies in development of efficient one-pot reactions and in generation of new 1-alkoxyindoles.<\/jats:p>","DOI":"10.3390\/molecules26051466","type":"journal-article","created":{"date-parts":[[2021,3,8]],"date-time":"2021-03-08T12:12:18Z","timestamp":1615205538000},"page":"1466","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["One-Pot Synthesis of Novel Multisubstituted 1-Alkoxyindoles"],"prefix":"10.3390","volume":"26","author":[{"given":"Ye Eun","family":"Kim","sequence":"first","affiliation":[{"name":"College of Pharmacy and Innovative Drug Center, Duksung Women\u2019s University, Seoul 01369, Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hyunsung","family":"Cho","sequence":"additional","affiliation":[{"name":"College of Pharmacy and Innovative Drug Center, Duksung Women\u2019s University, Seoul 01369, Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yoo Jin","family":"Lim","sequence":"additional","affiliation":[{"name":"College of Pharmacy and Innovative Drug Center, Duksung Women\u2019s University, Seoul 01369, Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Chorong","family":"Kim","sequence":"additional","affiliation":[{"name":"College of Pharmacy and Innovative Drug Center, Duksung Women\u2019s University, Seoul 01369, Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7764-7353","authenticated-orcid":false,"given":"Sang Hyup","family":"Lee","sequence":"additional","affiliation":[{"name":"College of Pharmacy and Innovative Drug Center, Duksung Women\u2019s University, Seoul 01369, Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2021,3,8]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"101","DOI":"10.1016\/S0065-2725(02)82027-X","article-title":"Recent advances in the chemistry of 1-hydroxytryptophans, and 1-hydroxytryptamines","volume":"82","author":"Somei","year":"2002","journal-title":"Adv. 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