Copper‐Mediated Direct Cyanatation of Benzamides: A New Approach to the Synthesis of Quinazolinediones. Issue 6 (5th February 2020)

• Record Type: Journal Article
• Authors: Kianmehr, Ebrahim; Falahat, Mohammad Reza; Tanbakouchian, Arezoo; Mahdavi, Mohammad
• Is Part Of: European journal of organic chemistry. Issue 6(2020)
• Page Start: 708
• Page End: 713
• Publication Date: 2020-02-05
• Subjects: Copper -- Cyanatation -- Benzamides -- Quinazolinediones -- Annulation; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201901567
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : Copper mediated cyanatation of N‐ (quinoline‐8‐yl)benzamides with cyanate salts and subsequent intramolecular cyclization of the resulting product was accomplished. Different derivatives of quinazoline‐2, 4(1 H, 3 H )‐dione bearing quinoline‐8‐yl directing group were readily prepared in moderate to high yields by this methodology from easily accessible starting materials through cascade directed C–H bond functionalization/annulation reactions. Abstract : A practical, versatile, and efficient copper‐mediated direct cyanatation of C–H bonds of N ‐(quinoline‐8‐yl)benzamides by potassium cyanate for the synthesis of quinazoline‐2, 4(1 H, 3 H )‐dione derivatives has been described. Various derivatives of quinazoline‐2, 4(1 H, 3 H )‐dione bearing quinoline‐8‐yl directing group were readily prepared in moderate to high yields by this methodology from easily accessible starting materials