Anionic [4+3] heteroannulation of 2-azidoacrylates: a modular synthesis of 2-benzazepin-1-ones.
نویسندگان
چکیده
2-Azidoacrylates undergo [4+3] annulation with phthalides under anionic conditions at low temperatures to furnish 5-hydroxy-2-benzazepinones, the formation of which represents a new concept for the construction of azepines as well as a new reactivity of 2-azidoacrylates.
منابع مشابه
Synthesis of 5-hydroxy-2,3,4,5-tetrahydro-[1H]-2-benzazepin-4-ones: selective antagonists of muscarinic (M3) receptors.
Two approaches to tetrahydro-[1H]-2-benzazepin-4-ones of interest as potentially selective, muscarinic (M(3)) receptor antagonists have been developed. Base promoted addition of 2-(tert-butoxycarbonylamino)methyl-1,3-dithiane with 2-(tert-butyldimethylsiloxymethyl)benzyl chloride gave the corresponding 2,2-dialkylated 1,3-dithiane which was taken through to the dithiane derivative of the parent...
متن کاملSynthesis of 2,3-Dimethoxy-7-methyl-7,12-dihydro-6H-[1]- benzofuro-[2,3-c]-[1]-benzazepin-6,12-dione
Treatment of 5,6-dimethoxy-2-(methylphenylcarbamoyl)-benzofuran-3carboxylic acid with PPA yielded 2,3-dimethoxy-7-methyl-7,12-dihydro-6H-[1]benzofuro-[2,3-c]-[1]-benzazepin-6,12-dione. The analogous 2-[(5,6-dimethoxybenzofuran-2-carbonyl)methylamino]benzoic acid was resistant to cyclization, whereas 2-[(6methoxybenzofuran-2-carbonyl)-amino]benzoic acid underwent cyclization to the corresponding...
متن کاملN,N,N,N-Tetramethylguanidinium acetate as an efficient and reusable ionic liquid catalyst for the one-pot synthesis of dihydropyrrol-2-ones
An extremely facile and efficient procedure which has been developed for the synthesis of dihydropyrrol-2-ones. One-pot four-component reaction of amines, dialkyl acetylenedicarboxylates and formaldehyde in the presence of N,N,N,N-tetramethylguanidinium acetate [TMG][Ac] in methanol at ambient temperature provides substituted dihydropyrrol-2-ones in good to high yields. The important aspects of...
متن کاملSynthesis of a 6-aryloxymethyl-5-hydroxy-2,3,4,5-tetrahydro-[1H]-2-benzazepin-4-one: a muscarinic (M3) antagonist.
A synthesis of the racemic 6-aryloxymethyl-5-hydroxy-2,3,4,5-[1H]-2-tetrahydrobenzazepin-4-one , for evaluation as a muscarinic (M(3)) antagonist, is described. 2-[2-tert-Butyldimethylsilyloxymethyl-6-(2,6-dimethoxyphenoxymethyl)phenyl]propan-2-ol was prepared from 2,6-dimethyl-1-bromobenzene and taken through to N-[3-(2,6-dimethoxyphenoxymethyl)-2-(propen-2-yl)phenyl]methyl-N-prop-2-enyl 2-nit...
متن کاملNovel GluN2B selective NMDA receptor antagonists: relative configuration of 7-methoxy-2-methyl-2,3,4,5-tetrahydro-1H-3-benzazepin-1-ols
The title compounds, C22H29NO2 (3) and C22H29NO2 (4) [systematic names: (1S*,2R*)-7-meth-oxy-2-methyl-3-(4-phenyl-but-yl)-2,3,4,5-tetra-hydro-1H-3-benzazepin-1-ol and (1R*,2R*)-7-meth-oxy-2-methyl-3-(4-phenyl-but-yl)-2,3,4,5-tetra-hydro-1H-3-benzazepin-1-ol, are diastereomers with the relative configuration of the adjacent hydroxyl and methyl groups at the seven-membered azepine ring being tran...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Chemical communications
دوره 48 33 شماره
صفحات -
تاریخ انتشار 2012