92345-90-9

Upstream product

• 18075-41-7 2-allyl-3-hydroxy-4-methoxybenzaldehyde 
• 74-83-9 methyl bromide 
• 74-88-4 methyl iodide 
• 18075-40-6 O-allylisovanillin 
• 621-59-0 isovanillin 
• 106-95-6 allyl bromide 

Downstream Products

• 374073-56-0 1-(2-allyl-3,4-dimethoxyphenyl)prop-2-en-1-ol 
• 469898-63-3 3,4-dimethoxy-1-(1'-hydroxyethyl)-2-(prop-2'-enyl)benzene 
• 66967-26-8 3,4-dimethoxy-2-(2-propenyl)phenol 
• 408340-61-4 2-allyl-3,4-dimethoxybenzyl alcohol 
• 550358-34-4 1-(2-allyl-3,4-dimethoxy-phenyl)-but-2-yn-1-ol 
• 778638-68-9 2-allyl-3,4-dimethoxy-1-vinylbenzene 
• 841301-94-8 1-(2-allyl-3,4-dimethoxyphenyl)-3-buten-1-ol 
• 885316-25-6 2-allyl-1-(dimethoxymethyl)-3,4-dimethoxybenzene 
• 934749-60-7 2-cyano-3-(2-allyl-3,4-dimethoxyphenyl)-1-propen-3-ol 
• 1000699-33-1 C₁₈H₂₆O₃ 
• 881199-41-3 2-allyl-1-[(2-allyl-3,4-dimethoxybenzyl)oxy]-3-ethoxy-4-methoxybenzene 
• 881199-39-9 2-allyl-1-[(2-allyl-3-ethoxy-4-methoxybenzyl)oxy]-3,4-dimethoxybenzene 
• 881199-40-2 2-allyl-1-[(2-allyl-3-isopropoxy-4-methoxybenzyl)oxy]-3,4-dimethoxybenzene 
• 57189-64-7 1,2-dimethoxynaphthalene 

Relevant academic research and scientific papers

TBuO 2H/Cu(acac) 2-Mediated Intramolecular Oxidative Lactonization of o -Allyl Arylaldehydes: Synthesis of 1-Oxoisochromans

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

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.).

Synthesis of Polysubstituted 3-Methylisoquinolines through the 6π-Electron Cyclization/Elimination of 1-Azatrienes derived from 1,1-Dimethylhydrazine

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.

CuI Mediated One-Pot Cycloacetalization/Ketalization of o-Carbonyl Allylbenzenes: Synthesis of Benzobicyclo[3.2.1]octane Core

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 2-hydroxymethyl-2,3-dihydrobenzofurans

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.

Synthesis of substituted indenes from isovanillin via claisen rearrangement and ring-closing metathesis

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

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.

Facile synthesis of substituted isoquinolines

A facile three-step protocol toward methoxy isoquinolines 7 starting with substituted 2-allylbenzaldehydes 9 was described. The overall synthetic process of skeleton 7 was carried out using the Grignard addition, PCC-oxidation, and one-pot oxidative cleavage of the olefinic group of skeleton 9 with OsO 4-NaIO4 followed by the condensation of the resulting 1,5-dicarbonyl compounds with NH4OAc. Skeleton 9 was prepared in high yield via the known Claisen rearrangement of skeleton 8 and O-methylation. Papaverine 2 is also synthesized via the simple three-step synthetic protocol.

Synthesis of tetrahydroanthracen-9-ones by the domino aldol condensation/Diels-Alder cycloaddition

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.

Synthesis of dihydrobenzoimidazo[2,1-a]isoquinolines

A one-pot protocol toward several substituted 5,6-dihydrobenzo[4,5] imidazo[2,1-a]isoquinolines 1 starting with 2-allylbenzaldehydes 2 was described. The process was carried out the one-pot condensation/hydroamination reaction of substituted 2-allylbenzaldehydes 2 with 1,2-diaminobenzenes 3 in refluxing toluene in good yields. Skeleton 2 was prepared via one-pot ortho-metalative PhBCl2-mediated double alkylation of hydroxybenzaldehyde 4 with LDA in moderate yields.