One-pot synthesis of three enaminones, (E)-1-(4-chlorophenyl)-3-morpholinoprop-2-en-1-one 1, (E)-1-(4-chlorophenyl)-3-(4-methylpiperazin-1-yl)prop-2-en-1-one 2, and ...(E)-1-(4-chlorophenyl)-3-(pyrrolidin-1-yl)prop-2-en-1-one 3 were achieved. The synthetic protocol via three components reaction of p-chloroacetophenone with DMFDMA (N,N-dimethylformamid-dimethylacetal) and the corresponding secondary amines (morpholine/N-methylpiperazine/pyrrolidine) in dioxane under heating for 2.5–4 h at 102 °C yielded the requisite enaminones. This protocol has the advantage of no separation of intermediate, no need for column purification with quantitative yield for the target compounds. The chemical features of the β-enaminones 1–3 were assigned by NMR. β-Enaminones 1, and 2 were assigned by single crystal X-ray diffraction technique. The intermolecular interactions in the crystal structures were analyzed quantitatively using Hirshfeld analysis. The Cl…H and O…H hydrogen bonds are common in both compounds while the C-H…π and N…H contacts are more significant in 2 than 1. DFT studies were investigated to show the electronic and spectroscopic properties (NMR and UV-Vis) of the studied systems.
Ethyl α-（dimethylaminomethylene）-2-cyanomethyl-4-phenylquinoline-3-carboxylate（2） as new synthons directed to 1-oxo-1,2-dihydrobenzob1,6naphthyridine-4-carbonitriles was obtained by the condensation ...of ethyl 2-cyanomethyl-4-phenylquinoline-3-carboxylate（1） and N,N-dimethylformamide dimethyl acetal（DMFDMA）.Reaction of this enamine with primary amines（3） in HOAc-DMF at120 ℃then affords 2-substituted 1-oxo-1,2-dihydrobenzob1,6naphthyridine-4-carbonitrile derivatives（4） in good yields by a tandem addition-elimination-cyclization reaction.
A novel approach to 1,2λ
5-azaphosphinines has been elaborated. Aminophosphonium chlorides bearing a β-dialkylaminocrotonic nitrile residue react with
N,
N-dimethylformamide dimethylacetal to afford ...1,2λ
5-azaphosphinines.
1-Cyano-2-N,N-dimethylformamidinylazulenes as new synthons directed to heterocycle-fused azulenes were obtained by the condensation of 2-amino-1-cyanoazulenes and N,N-dimethylformamide dimethyl ...acetal (DMFDMA). 1-Cyano-2-N,N-dimethylformamidinylazulene (2a) and 1-bromo-3-cyano-2-N,N-dimethylformamidinylazulene (2b) reacted with anilines (3a-h) to give 4-N-arylaminoazuleno-2,1-dpyrimidines in moderate yields. This reaction provides a new procedure for synthesis of pyrimidine-fused azulenes.
Celotno besedilo
Dostopno za:
BFBNIB, DOBA, GIS, IJS, IZUM, KILJ, KISLJ, NUK, PILJ, PNG, SAZU, UILJ, UKNU, UL, UM, UPUK
Two new imidazo1,2-
apyridine derivatives, pyridinoimidazo1,2-
apyridine (
10) and pyrroloimidazo1,2-
apyridine (
16), were synthesised from 2-amino-4-methyl-5-nitropyridine (
1) by linear ...cyclisation, making use of dimethylformamide dimethylacetal (DMFDMA) as an agent of vinylamine functionalisation. This report describes first the formation of pyridine and pyrroloimidazopyridine from (
1), and then the formation of pyridine-fused and pyrrolo-fused pyridine by the Friedländer method and reductive cyclisation followed by treatment of the resulting adduct with chloroacetaldehyde.
The reaction of 3,4-dihydroisoquinolin-1-yl-acetonitrile with DMFDMA afforded the enaminonitrile 5. Compound 5 was reacted with 2-aminobenzimidazole to yield 4-amino-3-(dihydroisoquinolin- ...1-yl)-benzo4,5imidazo1,2-apyrimidine (11) and with acetonitrile derivatives to afford pyrido2,1- aisoquinolines (15a - g).
Interaction of 2/(3)-methyl-3/(2)-vinylindoles and DMF·DMA/DMA·DMA at 110
°C led to the in situ generation of enamines, which on concurrent electrocyclization followed by subsequent aromatization ...afforded substituted carbazoles.
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