Regioselective electrophilic alkylation of anilines with phenylacetylene in the presence of montmorillonite KSF

Arienti, A.; Bigi, Franca; Maggi, Raimondo; Marzi, Elena; Moggi, P.; Rastelli, Massimo; Sartori, Giovanni; Tarantola, Fabio

doi:10.1016/s0040-4020(97)00100-2

Cited by 46 publications

(24 citation statements)

References 32 publications

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“…1‐Phenyl‐1‐(2‐aminophenyl)ethylene 20 and 1‐phenyl‐1‐(4‐aminophenyl)ethylene 21 were prepared by the reaction of phenylacetylene with aniline in the presence of KSF‐montmorillonite (Fluka) …”

Section: Methodsmentioning

confidence: 99%

Gas‐phase ion‐molecule reaction of alpha‐phenylvinyl cation towards substituted benzenes in the environment of an ITMS

Begala

Tocco

2011

J. Mass. Spectrom.

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Ion-molecule reactions between the α-phenylvinyl cation (α-PVC) and mono-substituted benzenes have been investigated using a quadrople ion-trap mass spectrometer. The α-PVC, generated by chemical ionization from phenylacetilene, was found to react selectively with mono-substituted benzenes bearing electron withdrawing groups to give the product ions [M + 103](+) and the trans-vinylating product ions [M + 25](+). To characterize the reaction products, a combination of collision-induced dissociation, isotope-labeling experiments and model compounds were used. The results indicate, in addition to direct heteroatom alkylation, high extent of ortho attack. We attributed the positional selectivity of the α-PVC to the nature of the substituent on the neutral molecule. In particular, hydroxy and amino groups promoted the alkenylation at ortho position.

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Section: Methodsmentioning

confidence: 99%

Gas‐phase ion‐molecule reaction of alpha‐phenylvinyl cation towards substituted benzenes in the environment of an ITMS

Begala

Tocco

2011

J. Mass. Spectrom.

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“…Ethyl 2-amino-4-fluorobenzoate, 9 2-(1-phenylethenyl)benzenamine (1b), 10 4-methoxy-2-(1-phenylethenyl)benzenamine (1d), 11 4,5-dimethoxy-2-(1-methylethenyl)benzenamine 11 5-chloro-2-(1-methylethenyl)benzenamine, 12 and ethyl 2-amino-3-methylbenzoate 14 were prepared by the appropriate reported methods. The IR spectra were recorded on a Shimadzu FTIR-8300 spectrometer.…”

Section: Methodsmentioning

confidence: 99%

“…t-butoxycarbonylation of 1d 11 -2-(1-methylethenyl) N-Methyl-4,5-dimethoxy-2-(1-methylethenyl) Typical Procedure for the Reduction of 6 to 7. 1,4,4-Trimethyl-1,4-dihydro-2H-3,1-benzoxazin-2one (7a).…”

Section: T-butyl N-[4-methoxy-2-(1-phenylethenyl)phenyl]carbamate (2dmentioning

confidence: 99%

Convenient Synthesis of 1,4-Dihydro-2H-3,1-benzoxazin-2-ones by Iodocyclization of t-Butyl 2-Vinylphenylcarbamate

Kobayashi¹,

Fukamachi²,

Nakamura³

et al. 2008

HETEROCYCLES

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It has been found that t-butyl 2-vinylphenylcarbamate derivatives underwent iodocyclization on treatment with iodine in the presence of sodium hydrogencarbonate to afford 4-iodomethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one derivatives in generally good yields. The reduction of these 4-iodomethyl derivatives with tributyltin hydride gave the corresponding 4-methyl derivatives in good yields.We previously demonstrated that the preparation of 4H-1,3-benzodioxin-2-one derivatives could be achieved by iodocyclization of t-butyl 2-vinylphenyl carbonate derivatives, derived from t-butoxycarbonylation of 2-vinylphenol derivatives. 1 As an extension of this cyclization reaction, we anticipated that a similar sequence starting with 2-aminostyrene derivatives should lead to formation of 1,4-dihydro-2H-3,1-benzoxazin-2-one derivatives. We report here on details concerning the results of our investigation which provide a new and simple method for constructing the 1,4-dihydro-2H-3,1benzoxazin-2-one skeleton. 2 Compounds having this skeleton have attracted considerable attention of medicinal and synthetic organic chemists, because some of them have been reported to exhibit a variety of biological activities, 3 such as HIV-1 reverse transcriptase inhibitory 3a and progesterone receptor antagonistic activities. 3b,e 1-Substituted 1,4-dihydro-2H-3,1-benzoxazin-2-one derivatives have been used as precursors for the generation of the corresponding aza-o-quinodimethane intermediates. 4 Most of the previous syntheses of 1,4-dihydro-2H-3,1-benzoxazin-2-one derivatives have been based on the reaction of 2-aminobenzyl alcohol derivatives with phosgene, 3,5,6 though Nishiyama, Naitoh, and Sonoda have recently reported a synthesis of 4-nonsubstituted derivatives by selenium-catalyzed carbonylation of 2-nitrobenzyl alcohols. 7 We conducted reactions of t-butyl 2-vinylphenylcarbamates (2), which were easily prepared by t-butoxycarbonylation of 2-aminostyrene derivatives (1) with di-t-butyl dicarbonate under the conditions

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“…2-(1-Arylethenyl)benzenamines 1a [5], 1c [6], 1d [7], 1f [5], 1g [5], 1h [8], and 1i [9] were prepared by the reported procedures. All other chemicals used in this study were commercially available.…”

Section: Experimental Partmentioning

confidence: 99%

Synthesis of 9,9‐Disubstituted 9H‐Pyrrolo[1,2‐a]indoles by Hydriodic Acid‐Catalyzed Cyclization of 1‐[2‐(1‐Aryl(or methyl)ethenyl)phenyl]‐1H‐pyrroles

Kobayashi

Hashimoto

et al. 2011

Helvetica Chimica Acta

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A novel method is reported for the synthesis of 9,9-disubstituted 9H-pyrrolo[1,2-a]indoles. Cyclization of 1-[2-(1-aryl(or methyl)ethenyl)phenyl]-1H-pyrroles, which can be easily prepared from 2-(1-aryl(or methyl)ethenyl)anilines, proceeds smoothly, in general, at 08 in the presence of a catalytic (or an equimolar) amount of HI in MeCN to provide the desired products.Introduction. -9H-Pyrrolo[1,2-a]indoles have attracted much attention due to their structural resemblance to cytostatic mytomycine derivatives [1]. Although a number of methods for the preparation of 9H-pyrrolo[1,2-a]indoles have recently been published [2], there have been only few reports on the synthesis of 9,9-disubstituted derivatives [1a] [3]. For example, Cartoon and Cheeseman have reported a synthesis 9,9-diphenyl-9H-pyrrolo[1,2-a]indole by the reaction of 1-(2-lithiophenyl)-1H-pyrrole with benzophenone, followed by acid-catalyzed cyclization of the resulting adducts [3]. Therefore, we embarked upon development of a convenient method for their preparation. In this article, we report that the hydriodic acid-catalyzed (or mediated) cyclization of 1-[2-(1-aryl(or methyl)ethenyl)phenyl]-1H-pyrroles 2 offers an efficient method for the preparation of 9,9-disubstituted 9H-pyrrolo[1,2-a]indoles 3.

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Regioselective electrophilic alkylation of anilines with phenylacetylene in the presence of montmorillonite KSF

Cited by 46 publications

References 32 publications

Gas‐phase ion‐molecule reaction of alpha‐phenylvinyl cation towards substituted benzenes in the environment of an ITMS

Gas‐phase ion‐molecule reaction of alpha‐phenylvinyl cation towards substituted benzenes in the environment of an ITMS

Convenient Synthesis of 1,4-Dihydro-2H-3,1-benzoxazin-2-ones by Iodocyclization of t-Butyl 2-Vinylphenylcarbamate

Synthesis of 9,9‐Disubstituted 9H‐Pyrrolo[1,2‐a]indoles by Hydriodic Acid‐Catalyzed Cyclization of 1‐[2‐(1‐Aryl(or methyl)ethenyl)phenyl]‐1H‐pyrroles

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