Abstract
An efficient method for the synthesis of 3-functionalized quinolines from commercially available acetophenones and anthranil has been described. Selectfluor propels the C(sp3)–H bond activation of the acetophenones and aza-Michael addition of anthranil resulting in annulated 3-acylquinolines in moderate to high yields. DMSO acts not only as a solvent but also as a one carbon donor in the reaction.
Highlights
The synthesis of quinolines has been an active area for many years and as a result, a number of efficient synthetic methods have been developed,[15,16,17,18,19,20] such as the classical Skraup,[21,22,23] Combes,[24,25,26] Friedlander,[27,28,29] Gould–Jacobs,[30,31,32] and Doebner–von Miller reactions.[33,34,35,36]
Dehydrogenation of saturated carbonyl compounds to afford a,b-unsaturated carbonyl derivatives has been found to be compatible with other organic transformations, leading to efficient one-pot protocols for the synthesis of functionalized molecules.[51,52,53,54]
Tiwari et al reported a similar reaction starting from saturated ketones and anthranils via sequential dehydrogenation/aza-Michael addition/ annulations cascade reactions in a one pot.[56]
Summary
Quinolines are one of the most ubiquitous structural units in natural products,[1,2,3,4,5] biologically active compounds[6,7,8,9,10,11] and functionalized materials (Fig. 1).[12,13,14] The synthesis of quinolines has been an active area for many years and as a result, a number of efficient synthetic methods have been developed,[15,16,17,18,19,20] such as the classical Skraup,[21,22,23] Combes,[24,25,26] Friedlander,[27,28,29] Gould–Jacobs,[30,31,32] and Doebner–von Miller reactions.[33,34,35,36] More recently, alternative strategies for the quinoline synthesis such as domino cycloadditions[37,38,39,40,41] and3-Acylquinolines have been reported to possess herbicidal activity[46] as well as antihypertensive activity.[47]. An efficient method for the synthesis of 3-functionalized quinolines from commercially available acetophenones and anthranil has been described. Selectfluor propels the C(sp3)–H bond activation of the acetophenones and aza-Michael addition of anthranil resulting in annulated 3-acylquinolines in moderate to high yields.
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
