Synthesis and modification of 4-hydroxy-2-methyl-3-(2-chloro-2-propenyl)quinoline

Avetisyan, A. A.; Aleksanyan, I. L.; Pivazyan, A. A.

doi:10.1134/s1070428006050150

Cited by 7 publications

(2 citation statements)

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“…13 Due to their biological relevance, a number of syntheses of furoquinolines and benzofuroquinolines have been reported. Avetisyan et al 14 reported a multistep synthesis of furo [3,2-c]quinolones in 20% overall yield based on the allylation of 4-hydroxy-2-methylquinoline with 2,3-dichloropropene and subsequent Claisen rearrangement.…”

Section: Introductionmentioning

confidence: 99%

Pyrrole versus quinoline formation in the palladium catalyzed reaction of 2-alkynyl-3-bromothiophenes and 2-alkynyl-3-bromofurans with anilines. A combined experimental and computational study

et al. 2012

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Benzofuroquinolines were prepared by a new type of Pd catalyzed annulation reaction. In the first step, 2-alkynyl-3-bromobenzofurans were prepared by Sonogashira reactions of 2,3-dibromobenzofuran. Their Pd catalyzed reaction with electron-rich anilines afforded benzofuroquinolines by a domino C-N coupling/annulation process. This reaction proceeds as a C,N-cyclization via the nitrogen atom and the ortho-carbon of the aniline. Similarly, furoquinolines were prepared from 2,3-dibromofuran. In contrast, benzofuropyrroles and furopyrroles were formed by N,N-cyclization when electron-poor anilines were used. Earlier, we reported results related to the thiophene and benzothiophene series. Quinolines were formed from 2,3-dibromobenzothiophene when electron rich anilines were used. In contrast, pyrroles were obtained in the case of electron-poor anilines. On the other hand, pyrroles were generally obtained, not depending on the type of aniline, when 2,3-dibromothiophene was employed as the starting material. In the present article, a detailed DFT study related to the mechanism (quinoline versus pyrrole formation) is reported which provides a rationalization of the selectivities observed for the furan, benzofuran, thiophene and benzothiophene series and for the different selectivities observed for electron-rich and -poor anilines.

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Section: Introductionmentioning

confidence: 99%

Pyrrole versus quinoline formation in the palladium catalyzed reaction of 2-alkynyl-3-bromothiophenes and 2-alkynyl-3-bromofurans with anilines. A combined experimental and computational study

et al. 2012

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“…Finally, this method was extended to the synthesis of 2,4dimethylfuro[3,2-c]quinoline (20). 16 3-Allyl-2-methylquinolin-4-ol (18), which we recently prepared, 17 underwent iodocyclization to give dihydrofuran derivative 19 11 in excellent yield. Dehydroiodination of 19, as described above, gave the desired product, as shown in Scheme 4.…”

Section: Scheme 1 Synthesis Of 3-ethoxycarbonylpyrrolesmentioning

confidence: 99%

Simple and Efficient Access to 3-Ethoxycarbonylpyrroles, Benzofurans, and Naphthofurans

Pancote¹,

Carvalho²,

Luchez³

et al. 2009

Synthesis

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