Synthesis of 4-substituted chlorophthalazines, dihydrobenzoazepinediones, 2-pyrazolylbenzoic acid, and 2-pyrazolylbenzohydrazide via 3-substituted 3- …

…, B Du, KP Faber, H Gunaydin, BL Hodous…

Index: Nguyen, Hanh Nho; Cee, Victor J.; Deak, Holly L.; Du, Bingfan; Faber, Kathleen Panter; Gunaydin, Hakan; Hodous, Brian L.; Hollis, Steven L.; Krolikowski, Paul H.; Olivieri, Philip R.; Patel, Vinod F.; Romero, Karina; Schenkel, Laurie B.; Geuns-Meyer, Stephanie D. Journal of Organic Chemistry, 2012 , vol. 77, # 8 p. 3887 - 3906

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Citation Number: 13

Abstract

Herein we describe a general three-step synthesis of 4-substituted chlorophthalazines in good overall yields. In the key step, N, N-dimethylaminophthalimide (8a) directs the selective monoaddition of alkyl, aryl, and heteroaryl organometallic reagents to afford 3-substituted 3- hydroxyisoindolinones 9b, 9i–9am. Many of these hydroxyisoindolinones are converted to chlorophthalazines 1b–1v via reaction with hydrazine, followed by chlorination with POCl3 ...