Photocyclizations of pharmacodynamic amines. V. Unusual rearrangements of the mescaline skeleton

The mescaline skeleton undergoes unusual rearrangements during photocyclization reactions. Irradiation of certain mescaline derivatives leads to products formed through unexpected bond cleavages and recombinations, rather than simple cyclization. The structures of the photoproducts were determined by spectroscopic methods and X-ray crystallography. The rearrangements involve migration of the trimethoxyphenyl group and formation of new carbon-nitrogen bonds, producing heterocyclic compounds not previously accessible by other routes. These findings illustrate the complexity of photochemical transformations in pharmacologically relevant amines and provide new synthetic pathways to novel ring systems.

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ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTPhotocyclizations of pharmacodynamic amines. V. Unusual rearrangements of the mescaline skeletonOsamu Yonemitsu, Hideo Nakai, Yuichi Kanaoka, Isabella L. Karle, and Bernhard WitkopCite this: J. Am. Chem. Soc. 1970, 92, 19, 5691–5700Publication Date (Print):September 1, 1970Publication History Published online1 May 2002Published inissue 1 September 1970https://pubs.acs.org/doi/10.1021/ja00722a025https://doi.org/10.1021/ja00722a025research-articleACS PublicationsRequest reuse permissionsArticle Views109Altmetric-Citations19LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts