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Khan, M. Niyaz; Ariffin, Azhar

doi:10.1023/a:1022590606020

Cited by 2 publications

(1 citation statement)

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“…HRMS calcd for C 9 H 7 NO 3 [M + H] + = 178.0499, [M + Na] + = 200.0318, found [M + H] + = 178.0517, [M + Na] + = 200.0337. Mp =139–140 °C (lit . mp =142–143 °C).…”

Section: Methodsmentioning

confidence: 99%

Synthesis of 4-Substituted Chlorophthalazines, Dihydrobenzoazepinediones, 2-Pyrazolylbenzoic Acid, and 2-Pyrazolylbenzohydrazide via 3-Substituted 3-Hydroxyisoindolin-1-ones

Nguyen¹,

Cee

Deak³

et al. 2012

J. Org. Chem.

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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 POCl(3). We have also discovered two novel transformations of 3-vinyl- and 3-alkynyl-3-hydroxyisoindolinones. Addition of vinyl organometallic reagents to N,N-dimethylaminophthalimide (8a) provided dihydrobenzoazepinediones 15a-15c via the proposed ring expansion of 3-vinyl-3-hydroxyisoindolinone intermediates. 3-Alkynyl-3-hydroxyisoindolinones react with hydrazine and substituted hydrazines to afford 2-pyrazolyl benzoic acids 16a-16d and 2-pyrazolyl benzohydrazides 17a-17g rather than the expected alkynyl phthalazinones.

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“…HRMS calcd for C 9 H 7 NO 3 [M + H] + = 178.0499, [M + Na] + = 200.0318, found [M + H] + = 178.0517, [M + Na] + = 200.0337. Mp =139–140 °C (lit . mp =142–143 °C).…”

Section: Methodsmentioning

confidence: 99%