374073-47-9Relevant 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.
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
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 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
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 substituted indenes from isovanillin via claisen rearrangement and ring-closing metathesis
Huang, Keng-Shiang,Wang, Eng-Chi
, p. 383 - 391 (2015/02/05)
A new synthesis of substituted indenes was studied. Based on Claisen rearrangement,Wittig reaction and ring-closing metathesis (RCM), a series of substituted indenes was synthesized from isovanillin in good yields.
One-pot access to 2-naphthols and benzofurans via the aerobic Wacker-type oxidation/intramolecular aldol cyclization
Chang, Meng-Yang,Chan, Chieh-Kai,Lin, Shin-Ying
, p. 1532 - 1538 (2013/02/25)
An aerobic Wacker-type oxidation/intramolecular aldol cyclization synthetic route toward two oxygenated 2-naphthols 3 and benzofurans 4 starting with skeleton 2 with good yields is described. The route has been carried by the one-pot transformation of the regioselective PdCl2/CuCl 2-mediated Wacker oxidative cyclization of skeleton 2 with molecular oxygen under the alkaline methanolic condition. Skeleton 2 was prepared from skeleton 1 in moderate total yields via the known protocol.
Synthesis of tetrahydroanthracen-9-ones by the domino aldol condensation/Diels-Alder cycloaddition
Chang, Meng-Yang,Wu, Ming-Hao
scheme or table, p. 3173 - 3177 (2012/08/13)
A facile protocol toward several substituted 3-aryl-3,4,4a,10-tetrahydro- 2H-anthracen-9-ones 1 starting with substituted 2-allylbenzaldehydes 2 was described. The overall synthetic process was carried out by the domino aldol condensation/Diels-Alder cycloaddition of skeleton 2 with substituted cinnamaldehydes 3 in an alkalic aqueous-methanolic solution followed by base-induced double migration of the resulting cycloadducts. Skeleton 2 was prepared from isovanillin (4) in moderate yield in five-steps via the known procedures with the synthetic sequence of O-allylation, Claisen rearrangement, O-methylation, Grignard methylation, and PCC-mediated oxidation.
Syntheses of substituted naphthalenes and naphthols
Huang, Keng-Shiang,Wang, Eng-Chi,Chen, Hsing-Ming
, p. 585 - 605 (2007/10/03)
Syntheses of substituted naphthalenes and naphthols are described. Based on Claisen rearrangement, ring-closing metathesis (RCM), and related reactions, isovanillin was successfully transformed into a series of substituted naphthalenes and naphthols with
Synthesis of substituted indenes from isovanillin via claisen rearrangement and ring-closing metathesis
Huang, Keng-Shiang,Wang, Eng-Chi
, p. 383 - 391 (2007/10/03)
A new synthesis of substituted indenes was studied. Based on Claisen rearrangement, Wittig reaction and ring-closing metathesis (RCM), a series of substituted indenes was synthesized from isovanillin in good yields.
