Efficient access to Unsymmetrically 3‐Substituted‐1, 10‐Phenanthrolines via Microwave Assisted Friedländer Condensation with Aldehydes. Issue 20 (9th December 2016)

• Record Type: Journal Article
• Authors: Dennison, Genevieve H.; White, Jonathan M.; Johnston, Martin R.
• Is Part Of: ChemistrySelect. Volume 1:Issue 20(2016)
• Page Start: 6434
• Page End: 6437
• Publication Date: 2016-12-09
• Subjects: Cyclisation -- Heterocycles -- Microwave Chemistry -- Organic Chemistry; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201601576
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: An efficient method with high conversion percentages (70 – 100 %) for the exclusive synthesis of unsymmetrical 3‐functionalised‐1, 10‐phenanthrolines via microwave assisted Friedländer condensation is presented. The method was applied to alkyl and aryl aldehydes and aldehydes containing terminal p ‐methoxybenzyl (PMB) protected hydroxyl moieties. Deprotection of the terminal alcohol yields 3‐alkyl hydroxy‐1, 10‐phenanthrolines containing flexible alkyl linkers which have previously not been achieved. These functionalised compounds constitute key intermediates for the synthesis of flexible, unhindered 1, 10‐phenanthroline based systems into the future. Abstract : An efficient method for the exclusive synthesis of unsymmetrical 3‐functionalised‐1, 10‐phenanthrolines via microwave assisted Friedländer condensation is presented. The method was applied to alkyl and aryl aldehydes and aldehydes containing terminal p ‐methoxybenzyl (PMB) protected hydroxyl moieties in high conversion percentages (70 – 100 %). Deprotection of the terminal alcohol yields 3‐alkyl hydroxy‐1, 10‐phenanthrolines containing flexible alkyl linkers which had previously not been achieved in the literature. These functionalised compounds constitute key intermediates for the synthesis of flexible, unhindered 1, 10‐phenanthroline based systems into the future.