Efficient Assembly of 1-(1<i>H</i>-Imidazol-1-yl)-3-methylene-1<i>H</i>-indenes via Tandem Reaction of (2-(Alkynyl)benzylidene)malonates with Imidazoles

Qiu, Guanyinsheng; Ding, Qiuping; Gao, Ke; Peng, Yiyuan; Wu, Jie

doi:10.1021/co100006g

Cited by 11 publications

(5 citation statements)

References 49 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In addition, other nucleophiles tested such as pyrrol, diisopropylamine, p -anisidine, phenylacetylene, and acetylacetone lead to no reaction or complex mixtures. Nevertheless, the methodology can be extended to the use of imidazoles as nucleophiles (Scheme , eq 2) . The transformation is again limited to the use of o -(alkynyl)benzylidenemalonates with aryl-substituted triple bonds and ocurrs with complete Z selectivity, leading to the corresponding products in high yields except for 1,3-dien-5-ynes with OMe substituents in the central aryl ring, which afford only moderate yields.…”

Section: Synthesis Of Five-membered Ringsmentioning

confidence: 99%

“…Nevertheless, the methodology can be extended to the use of imidazoles as nucleophiles (Scheme 52, eq 2). 144 The transformation is again limited to the use of o-(alkynyl)benzylidenemalonates with aryl-substituted triple bonds and ocurrs with complete Z selectivity, leading to the corresponding products in high yields except for 1,3-dien-5-ynes with OMe substituents in the central aryl ring, which afford only moderate yields.…”

Section: -Methyleneindanesmentioning

confidence: 99%

See 1 more Smart Citation

1,3-Dien-5-ynes: Versatile Building Blocks for the Synthesis of Carbo- and Heterocycles

et al. 2016

View full text Add to dashboard Cite

ABSTRACT:1,3-Dien-5-ynes have been extensively used as starting materials for the synthesis of a wide number of different carbo-and heterocycles. The aim of this review is to give an overview of their utility in organic synthesis, highlighting the variety of compounds that can be directly accessed from single reactions over these systems. Thus, cycloaromatization processes are initially commented, followed by reactions directed towards the syntheses of five-membered rings, other carbocycles and, finally, heterocycles. The diverse methodologies that have been developed for the synthesis of each of these types of compounds from 1,3-dien-5-ynes are presented, emphasizing the influence of the reaction conditions and the use of additional reagents in the outcome of the transformations.2

show abstract

Section: Synthesis Of Five-membered Ringsmentioning

confidence: 99%

Section: -Methyleneindanesmentioning

confidence: 99%

1,3-Dien-5-ynes: Versatile Building Blocks for the Synthesis of Carbo- and Heterocycles

et al. 2016

View full text Add to dashboard Cite

show abstract

“…2-[2-(Alkynyl)benzylidene]malonate undergoes a basecontrolled tandem reaction (nucleophilic addition and 5exocyclization) with imidazoles (Scheme 12). 105,106 The best yields and high Z-diastereoselectivity were obtained using t-BuOK, with no reaction occurring in the absence of base. Screening of solvents and additives (PdCl 2 , CuI, AgOTf, etc.)…”

Section: Domino Transformations Including Aza-michael Additionmentioning

confidence: 99%

Aza-Michael Addition of Imidazole Analogues

2016

View full text Add to dashboard Cite

show abstract

“…Transition-metal-catalyzed cyclization of ortho -substitued arenes has been investigated . Iodine-promoted and base-promoted cyclization reactions have been reported. Lewis and Brønsted acid-catalyzed reactions of alkene conjugate addition have been studied .…”

Section: Introductionmentioning

confidence: 99%

Sequential Knoevenagel Condensation/Cyclization for the Synthesis of Indene and Benzofulvene Derivatives

et al. 2021

View full text Add to dashboard Cite

Sequential Knoevenagel condensation/cyclization leading to indene and benzofulvene derivatives has been developed. The reaction of 2-(1-phenylvinyl)benzaldehyde with malonates gave benzylidene malonates, cyclized indenes, and dehydrogenated benzofulvenes. The product selectivity depends on the reaction conditions. The reaction with piperidine, AcOH in benzene at 80 °C for 1.5 h gave a benzylidene malonate in 75% yield as a major product. The reactions with piperidine, AcOH in benzene at 80 °C for 17 h and with TiCl 4 -pyridine at room temperature gave an indene derivative in 56 and 79% yields, respectively, as a major product. The reaction with TiCl 4 -Et 3 N gave a benzofulvene in 40% yield selectively. Indene was transformed to a benzofulvene derivative using the reagents TiCl 4 -Et 3 N and 2,3-dichloro-5,6dicyano-1,4-benzoquinone (DDQ). The reaction of variously substituted aryl derivatives with dimethyl malonate gave indene and benzofulvene derivatives. The reactions of 2-(1-phenylvinyl)benzaldehyde with Meldrum's acid or malononitrile also gave cyclized compounds in the suitable sequential or stepwise conditions. Furthermore, the reaction of 2-arylbenzaldehydes has been investigated. The limitation and scope have been described. The reaction mechanism of the cyclization steps has been examined by DFT calculations.

show abstract

Efficient Assembly of 1-(1H-Imidazol-1-yl)-3-methylene-1H-indenes via Tandem Reaction of (2-(Alkynyl)benzylidene)malonates with Imidazoles

Cited by 11 publications

References 49 publications

1,3-Dien-5-ynes: Versatile Building Blocks for the Synthesis of Carbo- and Heterocycles

1,3-Dien-5-ynes: Versatile Building Blocks for the Synthesis of Carbo- and Heterocycles

Aza-Michael Addition of Imidazole Analogues

Sequential Knoevenagel Condensation/Cyclization for the Synthesis of Indene and Benzofulvene Derivatives

Contact Info

Product

Resources

About