18075-41-7Relevant academic research and scientific papers
TBuO 2H/Cu(acac) 2-Mediated Intramolecular Oxidative Lactonization of o -Allyl Arylaldehydes: Synthesis of 1-Oxoisochromans
Chang, Meng-Yang,Lai, Kai-Xiang,Chen, Kuan-Ting
, p. 527 - 537 (2020/10/19)
A concise route for the tBuO 2H/Cu(acac) 2-mediated synthesis of 1-oxoisochromans is described. This includes: (i) oxidation of oxygenated o -allyl arylaldehydes and (ii) sequential intramolecular lactonization of the resulting olefin-containing benzoic acids. A plausible mechanism is proposed and discussed.
PdCl2/CuCl2/Bi(OTf)3-promoted Construction of Sulfonyl Dibenzooxabicyclo[3.3.1]nonanes and Arylnaphthalenes via Intramolecular Annulation of Sulfonyl o-Allylarylchromanones
Chang, Meng-Yang,Hsueh, Nai-Chen
supporting information, p. 5736 - 5750 (2020/12/01)
PdCl2/CuCl2/Bi(OTf)3-promoted intramolecular domino annulation of sulfonyl o-allylarylchromanones provides tetracyclic sulfonyl dibenzooxabicyclo[3.3.1]nonanes and bicyclic arylnaphthalenes with good to excellent yields in MeOH at room (25 °C) and refluxing (65 °C) temperature, respectively. The starting sulfonyl o-allylarylchromanones can be easily obtained from the intermolecular cyclocondensation of α-sulfonyl o-hydroxyacetophenones and o-allylbenzaldehydes. The uses of various catalysts and solvent systems are investigated herein for convenient transformation. A plausible mechanism is proposed and discussed. This protocol provides one-pot ring closure via carbon-carbon (C?C) bond formation. (Figure presented.).
Concise Synthesis of the ABC-Ring System of the Azafluoranthene, Tropoisoquinoline and Proaporphine Alkaloids: An Olefin Hydroacylation/Pomeranz-Fritsch Cyclization Approach
Vargas, Didier F.,Larghi, Enrique L.,Kaufman, Teodoro S.
, p. 2030 - 2038 (2019/04/26)
A straightforward approach toward a decorated cyclopenta[ ij ]isoquinoline embodying the ABC-ring system characteristic of the azafluoranthene (triclisine), tropoisoquinoline (pareitropone) and proaporphine (prodensiflorin B) alkaloids, is reported. The s
Diethylaminosulfur Trifluoride (DAST)-Mediated Intramolecular Benzannulation of o-Allylchalcones: Synthesis of 3-Fluorotetralins
Chang, Meng-Yang,Chen, Han-Yu,Tsai, Yu-Lin
, p. 2553 - 2563 (2019/06/08)
A concise route for the synthesis of 3-fluorotetralines is described, including: (i) NaBH 4 -mediated reduction of oxygenated o -allylchalcones and (ii) sequential DAST-mediated intramolecular annulation of the resulting alkenols. A plausible m
Biomimetic Syntheses of (±)-Isopalhinine A, (±)-Palhinine A, and (±)-Palhinine D
Chen, Chih-Ming,Shiao, Hui-Yi,Uang, Biing-Jiun,Hsieh, Hsing-Pang
supporting information, p. 15572 - 15576 (2018/11/10)
The first total synthesis of isopalhinine A, as well as unified syntheses of palhinine A and palhinine D, were successfully accomplished by means of a biomimetic strategy that proceeds through a bioinspired 5/6/6/9 tetracyclic intermediate, which mimics t
Synthesis of Polysubstituted 3-Methylisoquinolines through the 6π-Electron Cyclization/Elimination of 1-Azatrienes derived from 1,1-Dimethylhydrazine
Vargas, Didier F.,Larghi, Enrique L.,Kaufman, Teodoro S.
supporting information, p. 5605 - 5614 (2018/10/09)
A convenient one pot microwave-assisted 6π-electron cyclization/aromatization approach toward 3-methylisoquinolines is reported. The starting 1-azatriene derivatives were prepared in situ by reaction of 2-propenylbenzaldehydes with 1,1-dimethylhydrazine, which exhibited superior performance when compared with other hydrazine derivatives. Minor amounts of the related 3,4-dihydro isoquinolines were formed concomitantly with the isoquinolines, and a mechanism for their generation was proposed. The reaction conditions were optimized, and its scope and limitations were explored. In general, the transformation proceeded in moderate to good yields.
Synthesis of polyoxygenated dibenzo[a,e]cycloheptatrienes
Chan, Chieh-Kai,Chan, Yi-Ling,Tsai, Yu-Lin,Chang, Meng-Yang
, p. 2074 - 2088 (2017/03/17)
A successive route for the synthesis of substituted dibenzo[a,e]cycloheptatriene 1 was established by the reduction of 2-allylbenzaldehyde 4, the BF3·OEt2-mediated intermolecular coupling of 2-allylphenylmethanol 5 with oxygenated be
CuI Mediated One-Pot Cycloacetalization/Ketalization of o-Carbonyl Allylbenzenes: Synthesis of Benzobicyclo[3.2.1]octane Core
Chan, Chieh-Kai,Tsai, Yu-Lin,Chang, Meng-Yang
, p. 1870 - 1873 (2017/04/11)
CuI/DMSO-mediated intramolecular cycloacetalization/ketalization of o-carbonyl allylbenzenes has been achieved for constructing [6,6,5]-tricycles having a ketal motif in good yields. The expeditious one-step route provides a three C-O bond formation. The key products with the structural framework of a benzofused dioxabicyclo[3.2.1]octane core have been confirmed by X-ray crystallographic analysis. Synthesis of dihydroisocoumarin has been studied.
Synthesis of Substituted 2,3-Benzodiazepines
Chan, Chieh-Kai,Tsai, Yu-Lin,Chan, Yi-Ling,Chang, Meng-Yang
, p. 9836 - 9847 (2016/11/02)
A new, four-step synthetic route for substituted 2,3-benzodiazepines 1, starting from aldehyde 4, was developed with excellent overall yields. This route included the 1,2-addition of various aromatic Grignard reagents to 4, PCC oxidation, and aerobic Wacker-type oxidation of the olefinic group of 6, followed by condensation of the resulting 1,5-dicarbonyl 7 with N2H4. Isoquinolones 9 were obtained when an aldehyde group was used instead of a ketone. The key structures were confirmed by X-ray single-crystal diffraction analysis.
Synthesis of 2-hydroxymethyl-2,3-dihydrobenzofurans
Chang, Meng-Yang,Lin, Shin-Ying,Chanp, Chieh-Kai
, p. 1905 - 1912 (2014/08/18)
A one-pot protocol toward 2-hydroxymethyl-2,3-dihydrobenzofurans (1) starting with oxygenated o-allylbenzaldehydes (3) was described. The facile one-pot process was carried out by the oxidation of o-allylbenzaldehydes (3) with Oxone in the co-solvent of acetone and DMF in the presence of aqueous EDTA solution and then intramolecular ring-closure of the resulting o-allylphenols (2) in acceptable yields.
