4- -phthalazinone arylation

Phthalazinium-1-dates (196) are stable, yellow or colorless crystalline compounds that undergo an interesting variety of reactions. Reduction of aryl derivatives with zinc and dilute hydrochloric acid gives phthalimidines (210) whereas reduction with alkaline sodium hyposulfite gives 3-aryl-3,4-dihydro-l(2A)-phthalazinones (211)." 6.118-120,137 3 Mcthylphthal-... 

These substrates afford 4-alkyl(or aryl)-l(2//)-phthalazinones. The examples that follow are so numerous that they have been divided into groups according to the type of hydrazine used as synthon. 

Like the corresponding carboxylic acids, these substrates give 4-aIkyl(or aryl)-l(2//)-phthalazinone. However, the esters are seldom used simply because the acids are usually made more easily. An example of the use of keto esters is the condensation of ethyl 2-(2-methoxy-l-naphthoyl)benzoate (95) with hydrazine to afford 4-(2-methoxynaphthalen-l-yl)-l(27/)-phthalazinone (96) (neat H2NNH2-H2O, reflux, 4h 94%). ... 

These substrates, like their acid or ester counterparts, furnish 4-aIkyl(or aryl)-2(l/f)-phthalazinones. Although no keto amides have been so used in the more recent literature, some closely related o-acylbenzoyl azides have been employed. Thus o-benzoylbenzoyl azide (97) with hydrazine or phenylhydrazine gave 4-phenyl-l(2f/)-phthalazinone (98, R = H) (PhH, reflux, 2h 60%) or 2,4-diphenyl-l(2f/)-phthalazinone (98, R = Ph) (likewise 65%), respectively analogs were made similarly. ... 

Wang YF, Hsu T, Hay AS, Li K, Patel B. High temperature polymer blends of poly(aryl ether ketone phthalazinone). US Patent Application 20110104417, assigned to Polymics Ltd., State College, PA 2011. 

Y. Song, J. Wang, G. Li, Q. Sun, X. Jian, J. Teng, H. Zhang, Synthesis, characterization and optical properties of fluorinated poly(aryl ether)s containing phthalazinone moieties. Polymer 49 (23) (2008) 4995-5001. 

YE. Liang, Study on Sulfonated Poly(Aryl Ether)s Containing Phthalazinone Moieties as Proton Exchange Membranes (Doctoral degree paper), Dalian University of Technology, China, 2007. 

Poly(aryl ether ketone phthalazinone) PAEK, PAK, PEEK, PEKK, PBI, thermoplastic PI, PEL, PAES, PPS poly or their mixtures High-Tmiscible blends, with good processability. 7 = 108-365 C = 332-360°C 2011 58... 

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