93517-77-2Relevant academic research and scientific papers
NEW CONVENIENT ONE-STEP SYNTHESIS OF 4-ARYLPHTHALAZ-1-ONES
Ismail, M. Fekry,El-Bassiouny, F. A.,Younes, H. A.
, p. 2983 - 2984 (1984)
4-Arylphthalaz-1-ones (2a-e) are prepared by the hitherto unknown reaction of N-aminophthalimide (1) with aromatic hydrocarbons under Friedel-Crafts conditions.The reaction of N-aminophthalimide with Grignard reagents presents another convenient method for the synthesis of 4-alkyl or 4-arylphthalaz-1-ones.
Synthesis of 4-substituted chlorophthalazines, dihydrobenzoazepinediones, 2-pyrazolylbenzoic acid, and 2-pyrazolylbenzohydrazide via 3-substituted 3-hydroxyisoindolin-1-ones
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.
, p. 3887 - 3906 (2012/06/30)
Figure Persented: 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. 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.
SYNTHESIS AND BEHAVIOUR OF N-NAPHTHYLMETHYLENEAMINOPHTHALIMIDES TOWARD NUCLEOPHILIC REAGENTS
Kandile, Nadia Gharib
, p. 533 - 538 (2007/10/02)
The reactions of N-naphthylmethyleneaminophthalimides (1a, b) with Grignard reagents took place either by normal addition to one of the carbonyl groups to give 2a, d, or by 1,2-addition and cleavage to give 4-arylphthalaz-1-ones (4a-d).The reactions of 1a, b with amines gave 5, 6 and 7, respectively.
Action of Grignard Reagents and Amines on Some N-(Arylmethyleneamino)phthalimides
Ismail, M. Fekry,El-Bassiouny, F. A.,Enayat, E. I.,Kaddah, A. M.,Younes, H. A.
, p. 177 - 182 (2007/10/02)
N-(Arylmethyleneamino)phthalimides (2a-c) carrying an o-substituent in the aryl group were prepared by the reaction of N-aminophthalimide with o-substituted benzaldehydes.The reaction of these compounds with Grignard reagents proceeded either by normal addition to one of the carbonyl groups to give 3a-c or by addition and cleavage to give 4-arylphthalaz-1-ones 5a-c.The steric effect exhibited by either the Grignard reagent or the N-arylmethylene compound was studied.The reaction of N-furfurylideneaminophthalimide (2d) with Grignard reagents was also investigated.N-( Arylmethyleneamino)phthalimides reacted with primary amines to give N,N'-dialkylphthalamides (7a and b) while the reaction with secondary amines gave (8a and b).
