Heterocycles on a Gram Scale

  • Author: Vikki Cantrill
  • Published: 06 October 2015
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
  • Source / Publisher: Organic Letters/ACS Publications
  • Associated Societies: American Chemical Society (ACS), USA
thumbnail image: Heterocycles on a Gram Scale

An analysis of FDA-approved small-molecule drugs found that 21 % of them contain a saturated 6-membered ring with two heteroatoms, such as nitrogen or oxygen, within their structures. Consequently, new synthetic methods to produce these sorts of heterocycles are sought. Although a number of methods exist to synthesize 6-membered ring structures, such as morpholines and piperazines, and similar 7-membered ring compounds, such as azepines and oxazepines, often the use of expensive or toxic reagents detracts from their applicability in industry.

Eoghan McGarrigle, Varinder Aggarwal, and colleagues, University of Bristol, UK, and University College Dublin, Ireland, have developed a concise synthesis for substituted 6- and 7-membered ring systems. By reacting a substituted amino alcohol or diamine with a ring-forming reagent (α-phenylvinylsulfonium salt, cation pictured) and a base, the ring systems are formed with good selectivity and in moderate to excellent yields (27–75 %).

This highly practical route has many advantages that make it suitable for use in industry: reactions are conducted open to the air, solvents are not dried prior to use, and reactions can be performed on the gram scale.


Article Views: 3059

Sign in Area

Please sign in below

Additional Sign In options

Please note that to comment on an article you must be registered and logged in.
Registration is for free, you may already be registered to receive, e.g., the newsletter. When you register on this website, please ensure you view our terms and conditions. All comments are subject to moderation.

Article Comments - To add a comment please sign in

If you would like to reuse any content, in print or online, from ChemistryViews.org, please contact us first for permission and consult our permission guidance prior to making your request

Follow on Facebook Follow on Twitter Follow on YouTube Follow on LinkedIn Follow on Instagram RSS Sign up for newsletters

Magazine of Chemistry Europe (16 European Chemical Societies) published by Wiley-VCH