Bromoethylsulfonium Salt—A More Effective Annulation Agent for the Synthesis of 6- and 7-Membered 1,4-Heterocyclic Compounds

Yar, Muhammad; McGarrigle, Eoghan M.; Aggarwal, Varinder K.

doi:10.1021/ol8023727

Cited by 109 publications

(65 citation statements)

References 36 publications

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“…In 2012, Lin and colleagues reported a simple and efficient access to 1,1-cyclopropane aminoketones 12 via the reaction of α-aminoacetophenones 10 and vinylsulfonium salt 11 in the presence of 1,8-diazabicyclo [5.4.0]-undec-7-ene (DBU) 16) (Chart 4). The vinylsulfonium salt 11 was prepared from (2-bromoethyl) diphenylsulfonium trifluoromethanesulfonate (13) [17][18][19][20][21] by eliminating the hydrogen bromide with a base such as silver(I) oxide, 17,18) potassium bicarbonate, 19,22) or sodium hydride (NaH). 20) Recently, we developed a simple preparation of 2′-arylcyclohexane-1,3-dione-2-spirocyclopropanes 1 from 1,3-cyclohexanediones 8 directly using (1-aryl-2-bromoethyl) dimethylsulfonium bromides 14, which were converted into the corresponding vinylsulfonium salt in situ 23) (Chart 5).…”

Section: Resultsmentioning

confidence: 99%

An Efficient Method for the Synthesis of 2′,3′-Nonsubstituted Cycloalkane-1,3-dione-2-spirocyclopropanes Using (2-Bromoethyl)diphenylsulfonium Trifluoromethanesulfonate

Nambu

Ono

Hirota

et al. 2016

CHEMICAL & PHARMACEUTICAL BULLETIN

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An efficient and practical synthesis of 2′,3′-nonsubstituted cyclohexane-1,3-dione-2-spirocyclopropanes using a sulfonium salt was achieved. The reaction of 1,3-cyclohexanediones and (2-bromoethyl)diphenylsulfonium trifluoromethanesulfonate with powdered K 2 CO 3 in EtOAc at room temperature (r.t.) provided the corresponding spirocyclopropanes in high yields. The synthetic method was also applied to 1,3-cyclopentanedione, 1,3-cycloheptanedione, 1,3-indanedione, acyclic 1,3-diones, ethyl acetoacetate, and Meldrum's acid.

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Section: Resultsmentioning

confidence: 99%

An Efficient Method for the Synthesis of 2′,3′-Nonsubstituted Cycloalkane-1,3-dione-2-spirocyclopropanes Using (2-Bromoethyl)diphenylsulfonium Trifluoromethanesulfonate

Nambu

Ono

Hirota

et al. 2016

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Compound 1 and 5-(4-methylpyridin-2-yl)-1H-pyrazole-3-carboxylic acid for compound 2 were prepared by literature procedures [17][18] . When morpholine intermediates were not commercially available, they were prepared by two different methods [19][20] . Compound 2 and the analogs were prepared by amide coupling between 5-(4-methylpyridin-2-yl)-1H-pyrazole-3-carboxylic acid and the corresponding morpholines as described below.…”

Section: Chemical Synthesismentioning

confidence: 99%

Two distinct mechanisms of small molecule inhibition of LpxA acyltransferase essential for lipopolysaccharide biosynthesis

Han

Balibar

et al. 2019

Preprint

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This PDF file includes:Supplementary Methods Figs. S1 to S5 Tables S1 to S3 Supplementary Information Text Bacterial strains, plasmids, routine growth condition, and compound susceptibility testBacterial strains and plasmids used in this study are listed in Table S1. Miller's lysogeny broth (LB) 1 and LB-agar were used for routine growth and bacterial selection during plasmid construction. To maintain plasmids, 100 µg/mL ampicillin (Ap), 10 µg/mL chloramphenicol (Cm), and 50 µg/mL kanamycin (Km) were added to the media as needed. Compound susceptibility testing to determine MICs was performed in cation adjusted Mueller-Hinton II broth (CAMHB) according to CLSI protocols, as described previously 2 . To induce genes under the control of a lac promoter, 100 µM isopropyl β-D-1-thiogalactopyranoside (IPTG) was added to the media used in susceptibility testing. Compounds were synthesized at Novartis as described below. CHIR-090 was purchased from ChemScene (CS-0973). Spontaneous mutant selectionFor mutant selection with compound 1, cells in overnight culture of MG1655 ΔtolC were spread on LB agar containing 0.5 µg/mL compound 1. For mutant selection with compound 14, overnight culture of CDY0154 was used and the cells were spread on L-agar containing 16 and 32 µg/mL compound 14. Serial dilutions of the overnight culture were spread on LB agar to determine the number of cells (approximately 10 8 and 10 9 cells) used for selection. The LB agar plates were incubated overnight at 37 °C. Colonies arose and were streaked on fresh LB agar. After incubation overnight at 37 °C, a single colony of each mutant was grown in LB and stored in 15% glycerol at -80 °C for genome sequencing and susceptibility tests. The fabZ mutants were isolated from selection with inhibitors of LpxA and LpxD. Genome sequencing and mutation confirmationGenomic DNA for whole genome sequencing was isolated from E. coli strains using the Qiagen DNeasy Blood and Tissue kit with following the instruction for Gram-negative bacterial DNA. To sequence the genomes of isolated mutants, library preparation and sequencing reaction for next generation sequencing, and data analysis were performed using the Illumina Sample Preparation kits and Illumina Sequencer as described previously 2 . Sequencing reads were aligned to the reference E. coli MG1655 genome (Genbank ID: NC_000913.3) using bwa for determining single nucleotide polymorphisms and short insertion/deletions (indels, typically <10 bp). Mutations identified by genomics were confirmed by targeted PCR and Sanger sequencing. The primers were used to amplify the gene of interest with Phusion High-Fidelity PCR Master Mix with GC Buffer according to established protocols. Sequencing was performed by Elim BioPharma (Hayward, CA). The primers used for PCR and sequencing were TU117, TU243, TU276, TU332, TU475, TU503, TU504, TU512, and TU513. Construction of CDY0154The acrAB locus was replaced with the kanamycin resistant cassette (Km r ) using the λRED recombination system as described previously 3 . The DNA fragmen...

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“…[12] Also, a single-step synthesis of benzoxazepines has been reported in which N-tosyl-1,3-aminoalcohols were treated with bromoethylsulfonium salts, through vinyl sulfonium salt formation, which upon intramolecular cyclization provide 1,4-benzoxazepines. [13] Malonamide derivatives are some of the most important goals in synthetic chemistry because they display a number of interesting properties in various fields. [14] These compounds have some important applications such as effective liquid-liquid extractants, [15] poncoments in peptidomimetic substances, [16] excellent ionophores, [17] bidentate chelates and monomers in the nylon family.…”

Section: Introductionmentioning

confidence: 99%

Eco‐friendly synthesis of benzoxazepine and malonamide derivatives in aqueous media

Babazadeh

Hosseinzadeh‐Khanmiri

Zakhireh

2016

Applied Organom Chemis

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A special, efficient and reusable heterogeneous catalytic system is reported for the one-pot three-component synthesis of a series of malonamide and 2,3,4,5-tetrahydrobenzo[b] [1,4]oxazepine derivatives in the presence of a heterogeneous material composed of MCM-48/H 5 PW 10 V 2 O 40 in aqueous media and at room temperature. The products were identified using physical data (melting points) by comparison with those reported in the literature. Also, the structures of the new compounds were characterized by means of infrared, 1 H NMR, 13 C NMR and CHN analyses.

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Bromoethylsulfonium Salt—A More Effective Annulation Agent for the Synthesis of 6- and 7-Membered 1,4-Heterocyclic Compounds

Cited by 109 publications

References 36 publications

An Efficient Method for the Synthesis of 2′,3′-Nonsubstituted Cycloalkane-1,3-dione-2-spirocyclopropanes Using (2-Bromoethyl)diphenylsulfonium Trifluoromethanesulfonate

An Efficient Method for the Synthesis of 2′,3′-Nonsubstituted Cycloalkane-1,3-dione-2-spirocyclopropanes Using (2-Bromoethyl)diphenylsulfonium Trifluoromethanesulfonate

Two distinct mechanisms of small molecule inhibition of LpxA acyltransferase essential for lipopolysaccharide biosynthesis

Eco‐friendly synthesis of benzoxazepine and malonamide derivatives in aqueous media

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