Consecutive Three‐Component Synthesis of 2, 6‐Disubstituted Pyrimid‐4(3H)‐ones and 1, 5‐Disubstituted 3‐Hydroxypyrazoles Initiated by Copper(I)‐Catalyzed Carboxylation of Terminal Alkynes. Issue 14 (3rd September 2014)

• Record Type: Journal Article
• Authors: Schreiner, Ella; Braun, Stephan; Kwasnitschka, Christiane; Frank, Walter; Müller, Thomas J. J.
• Is Part Of: Advanced synthesis & catalysis. Volume 356:Issue 14/15(2014)
• Page Start: 3135
• Page End: 3147
• Publication Date: 2014-09-03
• Subjects: Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201400411
• Languages: English
• ISSNs: 1615-4150

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>A copper(I)‐catalyzed carboxylation of terminal alkynes followed trapping of the carboxylate with methyl iodide provides a straightforward access to 3‐substituted methyl propiolates that can be reacted in the same reaction vessel in a consecutive fashion to give 2, 6‐disubstituted pyrimid‐4(3<italic>H</italic>)‐ones and 1, 5‐disubstituted 3‐hydroxypyrazoles in moderate to good yields. The Cu(I)‐catalyzed carboxylation with carbon dioxide as C₁ source therefore provides an environmentally benign entry to three‐carbon building blocks in heterocyclic synthesis.</p> <p> <boxed-text content-type="graphic" position="anchor" orientation="portrait"> <graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgh1fbrpdv7" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /> </boxed-text> </p> </abstract>