DBU-catalyzed dearomative annulation of 2-pyridylacetates with α, β-unsaturated pyrazolamides for the synthesis of multisubstituted 2, 3-dihydro-4H-quinolizin-4-ones. Issue 1 (17th November 2021)

• Record Type: Journal Article
• Authors: Shen, Yao-Bin; Zhao, Jian-Qiang; Wang, Zhen-Hua; You, Yong; Zhou, Ming-Qiang; Yuan, Wei-Cheng
• Is Part Of: Organic chemistry frontiers. Volume 9:Issue 1(2022)
• Page Start: 88
• Page End: 94
• Publication Date: 2021-11-17
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d1qo01414e
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : DBU-catalyzed dearomative [3 + 3] annulation of 2-pyridylacetates and α, β-unsaturated pyrazolamides for the synthesis of multisubstituted 2, 3-dihydro-4 H -quinolizin-4-ones was developed. Abstract : The reaction of 2-pyridylacetates and α, β-unsaturated pyrazolamides with DBU as the catalyst has been developed. A range of unexplored multisubstituted 2, 3-dihydro-4 H -quinolizin-4-ones are obtained with satisfactory yields (up to 94%) and excellent diastereoselectivities (all cases >20 : 1 dr) via a dearomative [3 + 3] annulation process. This practical method also features transition metal free, mild reaction conditions, wide functional group tolerance, easy scale-up synthesis, and versatile further derivatization.