1H-1-Benzazepines. The reactions of laevulinic acid and β-benzoylpropionic acid with aniline and methoxyanilines

Abstract

Treatment of laevulinic acid with aniline yields 5-methyl-2,3-dihydro-lH-l-benzazepin-2-0ne and 5-(2-methyl-5-oxo-l-phenylpyrrolidin-2-yl)-4-oxo-N-phenylpentanamide In contrast, the reaction between P-benzoylpropionic acid and aniline yields 4-(2-0~0-1,5-dipheny1-2,3-dihydropyrrol-3-y1idene)-N,4-diphenylbutanamide, whose structure is confirmed by an independent synthesis. The yield of the latter type of reaction is enhanced if p-methoxyaniline is used, whereas the desired benzazepine is obtained if m-methoxyaniline is utilized. For example, the reaction between P-benzoylpropionic acid and m-methoxyaniline yields 8-methoxy-5-phenyl-2,3-dihydro-lH-l-benzazepine-2-one as the major cyclized product.

Intramolecular Aminolactonization for Synthesis of Furoindolin-2-One

“…Reagents and solvents were used without purification. Substrate 4 was synthesized by a reported method [12], and spectra data agreed with the literature values. A solution of 4 in THF was cooled to −78 • C, n-BuLi (1.6 M in n-hexane) was added, and the mixture was stirred for 30 min.…”

“…Reagents and solvents were used without purification. Substrate 4 was synthesized by a reported method [ 12 ], and spectra data agreed with the literature values.…”

“…We synthesized trisubstituted alkenes 2 and 6 bearing an alkoxycarbonyl group on the aniline nitrogen (Scheme 2). Aniline, its hydrochloride, and 4-oxopentanoic acid were condensed under heating at 200 • C to obtain lactam 4 according to the literature [12]. Thereafter, lactam 4 was transformed to imides 5a-e by treating n-butyllithium with alkyl chloroformate or triethylamine with Boc 2 O, after which imides 5 were hydrolyzed with NaOH in THF-water to prepare carboxylic acids 2a-e. Boc form 5c was solvolyzed with sodium methoxide in MeOH to obtain methyl ester 6.…”

Discovery of Oxime Ethers as Hepatitis B Virus (HBV) Inhibitors by Docking, Screening and In Vitro Investigation

“…Treatment of 3-aroylpropionic acids ( 2a , 2b and 2c ) with ethanol in the presence of p -toluenesulfonic acid provided ethyl 4-(4-substituted benzoyl)-4-oxobutanoate ( 3a , 3b and 3c ) in 94~96% yield. Compounds 4a , 4b , 4c , 5a , 5b and 5c were formed by the reaction of 3-aroylpropionic acids ( 2a , 2b and 2c ) with furfuryl alcohol or aniline in the presence of N , N -dicyclohexylcarbodiimide and 4-dimethylamioprdine in THF with yields of 88~96% [ 38 , 39 , 40 , 41 , 42 , 43 ]. The intermediate compounds ( 3a , 3b , 3c , 4a , 4b , 4c , 5a , 5b and 5c ) finally reacted with methoxylamine or hydroxylamine hydrochloride in pyridine and DCM to afford oxime ethers derivatives ( 3a-1 , 3a-2 , 3a-3 ; 3b-1 , 3b-2 , 3b-3 ; 3c-1 , 3c-2 , 3c-3 ; 4a-1 , 4a-2 , 4a-3 ; 4b-1 , 4b-2 , 4b-3 ; 4c-1 , 4b-2 , 4b-3 ; 5a-1 , 5a-2 , 5a-3 ; 5b-1 , 5b-2 , 5b-3 ; and 5c-1 , 5c-2 , 5c-3 ) as mixture of isomers.…”

“…The mixture was stirred and cooled to 0 °C and then N , N -dicyclohexylcarbodiimide (DCC) (1.1 equiv, 11 mmol) was added over a 5-min period and the reaction was stirred under anhydrous conditions for 6–8 h at room temperature. The mixture was filtered and the filtrate was evaporated to yield a crude product which was finally purified by recrystallization to give 4a , 4b , 4c , 5a , 5b and 5c as crystals [ 38 , 39 , 40 , 41 , 42 , 43 ].…”