Intramolecular Insertion of Acetylene into a Palladium−Carbon Bond in (Iminoacyl)palladium Complexes

Onitsuka, Kiyotaka; Segawa, Masaki; Takahashi, Shigetoshi

doi:10.1021/om9804125

Cited by 38 publications

(25 citation statements)

References 9 publications

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“…o -(Trimethylsilylethynyl)isocyanobenzene ( 3a ) was prepared in high yield from o -iodoaniline ( 1 ) and trimethylsilylacetylene via Sonogashira−Hagihara coupling and N -formylation, followed by dehydration (Scheme ) . The compound 3a could be isolated by silica gel column chromatography.…”

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confidence: 99%

New Access to 2,3-Disubstituted Quinolines through Cyclization of o-Alkynylisocyanobenzenes

1999

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o-Alkynylisocyanobenzenes underwent nucleophile-induced intramolecular cyclization to give 2,3-disubstituted quinoline derivatives in high yields. In addition to the oxygen and nitrogen nucleophiles such as methanol and diethylamine, the nucleophilic carbon of the enolate of malonate induced the cyclization effectively. Reaction of 1,4-di(trimethylsilylethynyl)-2,3-diisocyanobenzene with methanol afforded 2,9-dimethoxy-1,10-phenanthroline in good yield.

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confidence: 99%

New Access to 2,3-Disubstituted Quinolines through Cyclization of o-Alkynylisocyanobenzenes

1999

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“…[49] (Scheme 2a) Firstly, o-alkynylisocyanobenzene derivatives were prepared from the reaction of trimethylsilylacetylene and o-iodoaniline through Sonogashira-Hagihara coupling and N-formylation. [50] Next, the substrate 5a was treated with MeOH in the presence or absence of base K 2 CO 3 , resulted in six-membered substituted quinolines in excellent yields. In addition, according to the mechanistic investigation, the plausible mechanism is outlined in Scheme 2b.…”

Section: Radical Addition/cyclizationsmentioning

confidence: 99%

Radical Transformations towards the Synthesis of Quinoline: A Review

Teja

Khan

2020

Chemistry An Asian Journal

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Quinoline is considered one of the most ubiquitous heterocycles due to its engaging biological activities and synthetic utility over organic transformations. Over the past few decades, numerous reports have been documented in the synthesis of quinolines. The classical methods including, Skraup, Friedlander, Doebner‐von‐Miller, Conrad‐Limpach, Pfitzinger quinoline synthesis, and so forth, these are the well‐known methods to construct principal quinoline scaffold with several advantages and limitations. Recently, radical insertion or catalyzed reactions have emerged as a powerful and efficient tool to construct heterocycles with high atom efficiency and step economy. In this concern, this minireview mainly focused on the developments of Quinoline synthesis via radical reactions. In addition, a brief description of the preparation procedure, reactivity, and mechanisms is also included, where as possible. Respectively, the synthesis of quinolines is classified and summarized based on its reactivity, so it will help the researchers to grab the information in this exploration area, as Quinolines are promising pharmacophores.

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“…1). 23 The impossibility of 1,3-hydrogen shift explained the lack of aromatisation of the product. The isocyanide is inserted between the Pd-N 3 bond in the pallylpalladium azide K, generated in the reaction of Pd(0) with allylmethyl carbonate and TMSN 3 .…”

Section: Scheme 14mentioning

confidence: 99%