Facile Synthesis of Dihydroquinolines via Palladium Catalyzed Sequential Amination and Cyclisation of Morita-Baylis-Hillman Alcohols

Pambingal Rajan Sruthi; P Uma Sankar; Thachora Venu Saranya; Saithalavi Anas

doi:10.1002/slct.202003413

Facile Synthesis of Dihydroquinolines via Palladium Catalyzed Sequential Amination and Cyclisation of Morita-Baylis-Hillman Alcohols

ChemistrySelect. 2020 Nov 20;5(43):13598-13602. doi: 10.1002/slct.202003413. Epub 2020 Nov 18.

Authors

Pambingal Rajan Sruthi¹, P Uma Sankar², Thachora Venu Saranya¹, Saithalavi Anas^{1

3}

Affiliations

¹ School of Chemical Sciences Mahatma Gandhi University Kottayam Kerala India- 686560.
² Department of Chemistry Amrithaviswavidyapeet Kollam Kerala India- 690525.
³ Institute for Integrated Programmes & Research in Basic Sciences (IIRBS) Mahatma Gandhi University Kottayam Kerala India- 686560.

Abstract

Quinolines and its derivatives are significant class of heterocyclic compounds which are identified as the key component in many natural products and biologically important molecules. We describe herein a facile method for the synthesis of quinoline derivatives from Morita-Baylis-Hillman (MBH) Alcohols via Palladium Catalyzed intramolecular aryl amination followed by allylic amination pathway. The reaction between a series of MBH alcohols and amino compounds (Tosyl, aliphatic and aromatic amines) under optimized reaction conditions with Pd(PPh₃)₂Cl₂/DPPP catalyst system, afforded the corresponding 1,2-dihydroquinolines upto 95 % isolated yield.

Keywords: Allylicamination; Cyclization; Morita-Baylis-Hillman; Palladium; Quinoline.