97960-34-4

Upstream product

• 611-20-1 salicylonitrile 
• 106-95-6 allyl bromide 
• 6609-56-9 2-methoxy-benzonitrile 
• 74255-21-3 2-hydroxybenzonitrile sodium salt 
• 53638-81-6 2,2’-(4-amino-4H-1,2,4-triazole-3,5-diyl)diphenol 
• 14520-53-7 2-(prop-2'-enyloxy)benzamide 

Downstream Products

• 14520-53-7 2-(prop-2'-enyloxy)benzamide 
• 161562-67-0 (2-prop-2-enoxyphenyl)methanamine 
• 515163-37-8 3-allyl-2-hydroxybenzonitrile 
• 1054487-87-4 (2R)-1-(2-cyanophenoxy)-2,3-propanediol 
• 56715-37-8 (2S)-1-(2-cyanophenoxy)-2,3-propanediol 
• 515163-42-5 7-cyano-2-methylbenzo[b]furan 
• 93744-18-4 (S)-(+)-3-(2-cyanophenoxy)-1,2-epoxypropane 
• 46905-83-3 (S)-1-(2-cyanophenoxy)-2-hydroxy-3-tert-butylamino-propane 
• 850427-94-0 (R)-4-(2-cyanophenoxymethyl)-1,3,2-dioxathiolane-2,2-dioxide 
• 850427-88-2 (R)-4-(2-cyanophenoxymethyl)-1,3,2-dioxathiolane-2-oxide 
• 611-20-1 salicylonitrile 
• 65-45-2 salicylamide 

Relevant academic research and scientific papers

Palladium-Catalyzed Fluoroalkylative Cyclization of Olefins

A palladium-catalyzed fluoroalkylative cyclization of olefins with readily available Rf-I reagents to afford the corresponding fluoroalkylated 2,3-dihydrobenzofuran and indolin derivatives with moderate to excellent yields is reported. This novel procedure provides an efficient method for the construction of Csp3-CF2 and C-O/N bonds in one step. A wide range of functional groups are tolerated. It is proposed that a radical/SET (single electron transfer) pathway proceeding via the fluoroalkyl radical may be involved in the catalytic cycle.

Two ways of preparing benzonitriles using BrCCl3-PPh3 as the reagent

Benzamides were converted into benzonitriles with BrCCl3- PPh3-Et3N in CH2Cl2 in an Appel-type reaction. Benzaldoximes could be transformed to benzonitriles under identical conditions. It was found that the reaction system BrCCl3-(2 equiv.)PPh3 was also suitable for these transformations with PPh 3 replacing Et3N.

Surfactant-mediated solvent-free dealkylative cleavage of ethers and esters and trans-alkylation under neutral conditions

A simple, surfactant-mediated, one-pot, solvent-free dealkylative cleavage of aryl ethers and esters followed by subsequent optional trans-alkylation under essentially neutral conditions has been developed.

Asymmetric synthesis of aryloxypropanolamines via OsO4-catalyzed asymmetric dihydroxylation

A simple and effective procedure for the enantioselective synthesis of several β-adrenergic blocking agents incorporating the first asymmetric synthesis of celiprolol, is described. The key steps are (i) sharpless asymmetric dihydroxylation of aryl allyl ethers to introduce chirality into the molecules and (ii) conversion of cyclic sulfates into the corresponding epoxides using a three-step procedure.

A facile synthesis of benzofuran derivatives: A useful synthon for preparation of trypsin inhibitor

Mono-substituted 2-methylbenzo[b]furans were prepared by Claisen rearrangement of corresponding allyl phenyl ethers and subsequent bis(benzonitrile)palladium(II) chloride-mediated cyclization of o-allylphenols.

The stereochemistry of organometallic compounds. XLIII* rhodium-catalysed reactions of 2-(alkenyloxy)benzylamines and 2-(N-allyl-N-benzylamino)benzylamine

Reactions of 2-(allyloxy)benzylamines with H2/CO in the presence of rhodium catalysts give 1,3-benzoxazines, and 2-(N-allyl-N-benzylamino)benzylamine gives a quinazoline. These reactions have been shown to involve allylic cleavage followed by regioselective carbonylation at the internal carbon atom as demonstrated by crossover experiments. Reactions of longer chain (alkenyloxy)benzylamines under similar conditions give polymeric material.

Cyclizations and Rearrangements of Samarium Diiodide-Generated Vinyl Radicals

Vinyl bromides 1, 5, 15, 20, 23, 27, 33a,b, 41a-c, 44a-c, 46a,b, 52a,b, 55a, 56a,b, and 60a,b react with samarium diiodide in THF and/or acetonitrile to give the corresponding vinyl radicals.Radicals 3, 7, and 16 afforded products deriving from cyclization on the adjacent triple bond in a 5-(?-exo)exo, 6-(?-endo)exo, and 6-(?-exo)exo mode, respectively.Radical 7 undergoes competitive 1,5-hydrogen translocation.Vinyl radicals 21 and 24 readily cyclize on the proximal double bond, leading to 5- and 6-membered rings, respectively.Thienyl-substituted radical 28 leads to a product deriving from 5-exo cyclization on the thiophene ring and subsequent β-fission of the C-S bond, whereas thienyl-substituted radicals 34a,b undergo almost exclusively 1,5-hydrogen translocation.Aryl-substituted radicals obtained from vinyl bromides 41, 44, 46, 52, and 55 do not form any products deriving from 5-exo or 6-exo cyclization (or ipso cyclization).Finally, naphthyl-substituted radicals 57a and 61a give only direct reduction products, whereas the radical 61b affords, in addition to the direct reduction product, a rearranged product deriving from a 1,3-radical migration of the naphthylthio group.Evidence is reported for the reduction of EWG-substituted benzene rings and thio-substituted naphthalene rings to radical anions, which can fragment on the side chain with the elimination of allyl radicals. α-Oxy(and α-thio)-substituted radicals deriving from 1,5-shift rearrange to alcohols (and thiols) through a Wittig rearrangement or a cyclization/fragmentation process.

Asymmetric dihydroxylation of aryl allyl ethers

Asymmetric dihydroxylation of substituted aryl allyl ethers is described. Para-substituents are shown to favor high enantioselectivity (89-95%ee), while ortho-groups have a deleterious effect (28-63%ee). Four medicinal agents were prepared: guaifenesin (expectorant), mephenesin (muscle relaxant), chlorphenesin (antifungal) and propanolol (β-blocker).

On the Lead Tetraacetate Oxidation of 4-Amino-1,2,4-triazoles, 1-Amino- and 2-Amino-1,2,3-triazoles

Lead tetraacetate oxidation of 4-amino-1,2,4-triazoles, 1-amino- and 2-amino-1,2,3-triazoles affords mainly fragmentation to nitriles or acetylenes, even in the presence of intramolecularly attached double bonds. - Keywords: Lead tetraacetate; N-Nitrenes; 4-Amino-1,2,4-triazoles; 1-Amino-1,2,3-triazoles; 2-Amino-1,2,3-triazoles