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However, this method typically requires heating highly reactive aminoacrylates or activated carbonyl compounds, such as \u03b2\u2010ketoesters. In this study, we discovered that the addition of ammonium fluoride to various cyclic ketones enables the efficient synthesis of cycloalkane\u2010fused pyridines under mild conditions. The optimal conditions established in this study exhibit a wide range of substrate generality. Furthermore, the reaction conditions were found to be selective for cyclic ketones in preference to aliphatic ketones. In addition, this reaction has been successfully applied to the synthesis of epiguaipyridine, a natural product, and aza[5]helicene, a functional molecule.<\/jats:p>","DOI":"10.1002\/chem.202500298","type":"journal-article","created":{"date-parts":[[2025,3,18]],"date-time":"2025-03-18T06:30:33Z","timestamp":1742279433000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Modified Bohlmann\u2013Rahtz Pyridine Synthesis for Cyclic Ketones"],"prefix":"10.1002","volume":"31","author":[{"given":"Keita","family":"Ikeno","sequence":"first","affiliation":[{"name":"Graduate School of Pharmaceutical Sciences Chiba University  1\u20108\u20101, Inohana, Chuo\u2010ku Chiba 260\u20138675 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Haruna","family":"Oku","sequence":"additional","affiliation":[{"name":"Graduate School of Pharmaceutical Sciences Chiba University  1\u20108\u20101, Inohana, Chuo\u2010ku Chiba 260\u20138675 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7905-0961","authenticated-orcid":false,"given":"Kenta","family":"Rakumitsu","sequence":"additional","affiliation":[{"name":"Graduate School of Pharmaceutical Sciences Chiba University  1\u20108\u20101, Inohana, Chuo\u2010ku Chiba 260\u20138675 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mariko","family":"Kitajima","sequence":"additional","affiliation":[{"name":"Graduate School of Pharmaceutical Sciences Chiba University  1\u20108\u20101, Inohana, Chuo\u2010ku Chiba 260\u20138675 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3884-2583","authenticated-orcid":false,"given":"Hayato","family":"Ishikawa","sequence":"additional","affiliation":[{"name":"Graduate School of Pharmaceutical Sciences Chiba University  1\u20108\u20101, Inohana, Chuo\u2010ku Chiba 260\u20138675 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,3,26]]},"reference":[{"key":"e_1_2_7_1_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00965a040"},{"key":"e_1_2_7_1_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jafc.6b00680"},{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1139\/v79-180"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.6b00076"},{"key":"e_1_2_7_3_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.dyepig.2019.05.004"},{"key":"e_1_2_7_3_3","doi-asserted-by":"publisher","DOI":"10.1002\/adma.201204961"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.4c01122"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr500099b"},{"key":"e_1_2_7_5_2","doi-asserted-by":"publisher","DOI":"10.1002\/slct.202203668"},{"key":"e_1_2_7_5_3","doi-asserted-by":"publisher","DOI":"10.1002\/tcr.202200099"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1002\/cber.19570901021"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja994247b"},{"key":"e_1_2_7_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja110166x"},{"key":"e_1_2_7_7_3","doi-asserted-by":"publisher","DOI":"10.1039\/D1OB02145A"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr0300441"},{"key":"e_1_2_7_9_1","doi-asserted-by":"publisher","DOI":"10.1039\/b203397f"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo048106q"},{"key":"e_1_2_7_11_1","first-page":"2459","volume":"16","author":"see R.","year":"2007","journal-title":"Synlett"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo900950x"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201606496"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b04038"},{"key":"e_1_2_7_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.2c02587"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1097-0045(1996)6 <88::AID-PROS17>3.0.CO;2-N"},{"key":"e_1_2_7_16_1","doi-asserted-by":"publisher","DOI":"10.1016\/0022-4731(77)90040-1"},{"key":"e_1_2_7_17_1","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.200900125"},{"key":"e_1_2_7_17_2","doi-asserted-by":"publisher","DOI":"10.1248\/cpb.60.213"},{"key":"e_1_2_7_18_1","doi-asserted-by":"publisher","DOI":"10.1021\/np0005208"},{"key":"e_1_2_7_18_2","doi-asserted-by":"publisher","DOI":"10.3987\/COM-20-14394"},{"key":"e_1_2_7_19_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200600414"},{"key":"e_1_2_7_19_2","doi-asserted-by":"publisher","DOI":"10.1098\/rsos.172037"},{"key":"e_1_2_7_19_3","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2020.151837"},{"key":"e_1_2_7_19_4","doi-asserted-by":"publisher","DOI":"10.1039\/D1OB01299A"},{"key":"e_1_2_7_19_5","first-page":"7904","volume":"9","author":"Holliday H. 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