13580-91-1Relevant academic research and scientific papers
Regioselective Synthesis of Substituted 4-Alkylamino and 4-Arylaminophthalazin-1(2 H)-ones
Krishnananthan, Subramaniam,Smith, Daniel,Wu, Dauh-Rurng,Yip, Shiuhang,Gunaga, Prashantha,Mathur, Arvind,Li, Jianqing
, p. 1520 - 1526 (2016/03/01)
(Chemical Equation Presented). An efficient regioselective synthesis of substituted 4-alkylamino and 4-arylaminophthalazin-1(1H)-ones 5 is described. This new method features the formation of substituted phthalazin-1(1H)-ones 3 by the reaction of 2-formylbenzoic acids 1 or 3-hydroxyisobenzofuran-1(3H)-ones 2 with hydrazine to generate phthalazin-1(2H)-ones 3. Subsequent regioselective bromination of phthalazin-1(2H)-ones 3 with benzyltrimethylammonium tribromide (BTMA-Br3) followed by mixed copper-copper oxide-catalyzed amination of 4-bromophthalazin-1(2H)-ones 4 with primary amines generates aminophthalazin-1(2H)-ones in good overall yields.
AMINOPHTHALAZINONE DERIVATIVES, VII REACTION OF CHLOROPHTHALAZINONE WITH SECONDARY AMINES STUDY OF THE STERIC EFFECT, II
Koermendy, K.,Ruff, F.
, p. 155 - 166 (2007/10/02)
In the aminolysis of chlorophthalazinone (1a) with secondary amines, the yield of N-substitution (1 5, 1 7) is significantly affected by the steric structure of the amine.In the cyclic secondary amines substituents at the C-2 position give rise to a strong steric hindrance.The possibility for N-substitution gradually decreases with increasing size of the ring, while in the case of open-chain secondary amines it varies suddenly as a function of the position of the NH group in the chain.
