Traceless Solid-Phase Synthesis of Substituted Benzimidazolones

Wang, Chih Chung; Li, Wen Ren

doi:10.1021/cc049926j

Cited by 8 publications

(3 citation statements)

References 40 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The subsequent reduction of the nitro group to the amino triggered the final cyclative cleavage from the carbamate linkage. The traceless synthesis of benzimidazolones exploited a substituted 1-fluoro-2-nitrobenzene connected via carbamate 656 (Scheme ) to Wang resin 2 . The cyclative cleavage to benzimidazolones 657 occurred simultaneously with the reduction of the nitro group.…”

Section: Cyclative Cleavagementioning

confidence: 99%

Traceless Solid-Phase Organic Synthesis

2019

View full text Add to dashboard Cite

Traceless solid-phase synthesis represents an ultimate sophisticated synthetic strategy on insoluble supports. Compounds synthesized on solid supports can be released without a trace of the linker that was used to tether the intermediates during the synthesis. Thus, the target products are composed only of the components (atoms, functional groups) inherent to the target core structure. A wide variety of synthetic strategies have been developed to prepare products in a traceless manner, and this review is dedicated to all aspects of traceless solid-phase organic synthesis. Importantly, the synthesis does not need to be carried out on a linker designed for traceless synthesis; most of the synthetic approaches described herein were developed using standard, commercially available linkers (originally devised for solid-phase peptide synthesis). The type of structure prepared in a traceless fashion is not restricted. The individual synthetic approaches are divided into eight sections, each devoted to a different methodology for traceless synthesis. Each section consists of a brief outline of the synthetic strategy followed by a description of individual reported syntheses.

show abstract

Section: Cyclative Cleavagementioning

confidence: 99%

Traceless Solid-Phase Organic Synthesis

2019

View full text Add to dashboard Cite

show abstract

“…Heating the suspension of 139 in trimethylorthoformate, followed by cleavage from the resin, gave the benzoimidazole 141 (72-84% yield). Wang et al 90 reported the solid-phase synthesis of benzimidazolones after the introduction of one of the nitrogens by nucleophilic substitution of a carbamate to an o-fluoronitrobenzene and spontaneous cyclization and detachment from the resin under reductive conditions.…”

Section: Benzoannelated Five-membered Heterocyclesmentioning

confidence: 99%

Solid-Phase Synthesis of Biologically Active Benzoannelated Nitrogen Heterocycles: An Update

2008

View full text Add to dashboard Cite

show abstract

“…Spontaneous cyclization and detachment of the benzimidazolones (122) from the resin (121) occurs under reductive conditions on solid-support. To incorporate a third element of diversity, benzimidazolones (122) were treated with NaH and various alkyl halides in DMF to afford fully functionalized benzimidazolones (123) (Scheme 23) [129].…”

Section: Benzimidazolonesmentioning

confidence: 99%

Recent Advances in the Solid-Phase Combinatorial Synthetic Strategies for the Quinoxaline, Quinazoline and Benzimidazole Based Privileged Structures

Kamal¹,

Reddy²,

Devaiah

et al. 2006

MRMC

View full text Add to dashboard Cite

Quinoxaline, quinazoline and benzimidazole based templates have been synthesized on solid-support employing different methodologies. This review enlightens academic and industrial examples of combinatorial synthesis for this type of heterocycles that appeared in the literature in the last decade. Hence, some of the important synthetic strategies for the generation of quinoxaline, quinazoline and benzimidazole based privileged structures, and the important biological activities for these heterocycles have been highlighted. Further, benzothiadiazinone, thioxoquinazolinone, cinnoline and indazole are also examined in this review.

show abstract

Traceless Solid-Phase Synthesis of Substituted Benzimidazolones

Cited by 8 publications

References 40 publications

Traceless Solid-Phase Organic Synthesis

Traceless Solid-Phase Organic Synthesis

Solid-Phase Synthesis of Biologically Active Benzoannelated Nitrogen Heterocycles: An Update

Recent Advances in the Solid-Phase Combinatorial Synthetic Strategies for the Quinoxaline, Quinazoline and Benzimidazole Based Privileged Structures

Contact Info

Product

Resources

About