Regio- and stereoselective synthesis of 1-(1-halovinyl)-1H-indoles from 1-ethynyl-1H-indoles with in situ generated HX

Sato, Akihiro; Ohashi, Kazuhiro; Ito, Kouhei; Iwasawa, Tetsuo

doi:10.1016/j.tetlet.2013.03.107

Cited by 19 publications

(7 citation statements)

References 58 publications

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“…[18] Corresponding TCBD 30 was obtained in av ery good yield of 83 %. This experiment completes the ob- [19] also underwent the reaction and provided TCBD 32 in 59 %yield. Concerning the formation of both TCBDs 30 and 32,nobyproducts were isolated.…”

Section: Resultssupporting

confidence: 64%

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Reactivity of Functionalized Ynamides with Tetracyanoethylene: Scope, Limitations and Optoelectronic Properties of the Adducts

Betou

Durand

Sallustrau

et al. 2017

Chemistry An Asian Journal

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The reactivity of functionalized ynamides and arylynamines with tetracyanoethylene at room temperature was evaluated. In most cases, the corresponding 1,1,4,4-tetracyanobutadienes (TCBDs) were obtained in good to excellent yields through a [2+2]-cycloaddition/[2+2]-retro-electrocyclization sequence. The influence of diverse functional groups on the yield of the reaction was investigated, in particular concerning multiple ynamides. These TCBDs were characterized by various spectroscopic techniques and electrochemistry and X-ray diffraction in some cases.

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Section: Resultssupporting

confidence: 64%

“…This experiment completes the observation recently made by Kato and collaborators that carbazole is also a good activating group for initiating CA‐RE with TCNE . Similarly, indole ynamine 31 also underwent the reaction and provided TCBD 32 in 59 % yield. Concerning the formation of both TCBDs 30 and 32 , no byproducts were isolated.…”

Section: Resultsmentioning

confidence: 99%

Reactivity of Functionalized Ynamides with Tetracyanoethylene: Scope, Limitations and Optoelectronic Properties of the Adducts

Betou

Durand

Sallustrau

et al. 2017

Chemistry An Asian Journal

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“…The starting N -alkynylindoles 1 were readily available by using the copper-catalyzed coupling reaction between indoles with haloalkynes . Following our knowledge that lithium anions react easily with elemental selenium to form selenolates, which can reduce triple bonds via hydroselenation, the lithiation of N -alkynylindole 1a (0.5 mmol) was initially carried out by the addition of n -butyllithium (1.2 equiv) in THF (3 mL) at −78 °C for 10 min, under an inert atmosphere, and then the mixture was warmed to 0 °C while stirring for 30 min at this temperature.…”

Section: Resultsmentioning

confidence: 99%

“…Reagents and solvents were handled using standard syringe techniques. The starting N -alkynylindoles 1 were readily available by using the copper-catalyzed coupling reaction between indoles with haloalkynes …”

Section: Methodsmentioning

confidence: 99%

Synthesis of 3-(Organochalcogen) Chalcogenazolo Indoles via Cascade Cyclization of N-Alkynylindoles

et al. 2019

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A transition metal-free one-pot, three-steps protocol combining N-alkynylindoles, n-butyllithium, elemental selenium, and an electrophile source was developed to allow the synthesis of 3-(organoselanyl) selenazolo indoles. Substrate scope was studied by varying the structure of Nalkynylindoles and the electrophile source. This sequential reaction proceeded selectively through an initial intramolecular 5-endo-dig mode with two new carbon−selenium bonds formation in a one-pot procedure. The reaction conditions were also compatible with elemental sulfur and tellurium, which led to construct 3-(alkylthio) thiazolo indoles and 3-(alkyltelluro) tellurazolo indoles, respectively. In addition, it was also demonstrated that a series of dichalcogenides derived from chalcogenazoloindoles ring could be easily prepared via oxidation of chalcogenolate anion in contact with air.

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“…The participation of terminal N -alkynyl azoles in Sonogashira coupling reactions can be complicated by alternative, palladium-catalyzed hydroalkynylation reactions (see Section 3.2.2). However, as part of their work investigating the structure-activity relationship of ethynyl purines and analogues as BCL-ABL inhibitors, Huang and co-workers at ARIAD Pharmaceuticals prepared a series of N 9 -alkynyl purines 123 and 124 by Sonogoshira coupling of the N -ethynyl purine 121 with the aryl iodides 122 , albeit in very low yield (Scheme 35) [62].…”

Section: Reactions Of N-alkynyl Azolesmentioning

confidence: 99%

Preparation and Utility of N-Alkynyl Azoles in Synthesis

Reinus

Kerwin

2019

Molecules

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Heteroatom-substituted alkynes have attracted a significant amount of interest in the synthetic community due to the polarized nature of these alkynes and their utility in a wide range of reactions. One specific class of heteroatom-substituted alkynes combines this utility with the presence of an azole moiety. These N-alkynyl azoles have been known for nearly 50 years, but recently there has been a tremendous increase in the number of reports detailing the synthesis and utility of this class of compound. While much of the chemistry of N-alkynyl azoles mirrors that of the more extensively studied N-alkynyl amides (ynamides), there are notable exceptions. In addition, as azoles are extremely common in natural products and pharmaceuticals, these N-alkynyl azoles have high potential for accessing biologically important compounds. In this review, the literature reports of N-alkynyl azole synthesis, reactions, and uses have been assembled. Collectively, these reports demonstrate the growth in this area and the promise of exploiting N-alkynyl azoles in synthesis.

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Regio- and stereoselective synthesis of 1-(1-halovinyl)-1H-indoles from 1-ethynyl-1H-indoles with in situ generated HX

Cited by 19 publications

References 58 publications

Reactivity of Functionalized Ynamides with Tetracyanoethylene: Scope, Limitations and Optoelectronic Properties of the Adducts

Reactivity of Functionalized Ynamides with Tetracyanoethylene: Scope, Limitations and Optoelectronic Properties of the Adducts

Synthesis of 3-(Organochalcogen) Chalcogenazolo Indoles via Cascade Cyclization of N-Alkynylindoles

Preparation and Utility of N-Alkynyl Azoles in Synthesis

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