39900-63-5

Usage

Synthesis Reference(s)

Synthetic Communications, 20, p. 71, 1990 DOI: 10.1080/00397919008054617

InChI:InChI=1/C8H7NO2/c1-11-7-3-2-6(5-9)8(10)4-7/h2-4,10H,1H3

Upstream product

• 17580-69-7 2-hydroxy-5-methoxybenzaldehyde oxime 
• 108-24-7 acetic anhydride 
• 556-64-9 methyl thiocyanate 
• 150-76-5 4-methoxy-phenol 
• 545-06-2 trichloroacetonitrile 
• 1056956-14-9 Acetic acid 2-cyano-4-methoxy-phenyl ester 
• 39835-06-8 5-methoxybenzo[d]isoxazole 
• 672-13-9 2-hydroxy-5-methoxybenzaldehyde 
• 55305-43-6 N-cyano-N-phenyl-p-toluenesulfonamide 
• 66384-65-4 (E)-5-methoxy-2-hydroxybenzaldehyde oxime 

Downstream Products

• 1072878-84-2 (3-amino-5-methoxybenzofuran-2-yl)(3,4,5-trimethoxy-phenyl)methanone 
• 705290-50-2 2-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propoxy]-5-methoxy-benzonitrile 
• 1033834-86-4 2-{6-[4-(4-amino-5-fluoro-pyrimidin-2-yloxy)-piperidin-1-yl]-5-fluoro-pyrimidin-4-yloxy}-5-methoxy-benzonitrile 
• 1033833-98-5 2-{6-[4-(4-amino-5-fluoro-pyrimidin-2-yloxy)piperidin-1-yl]-pyrimidin-4-yloxy}-5-methoxy-benzonitrile 
• 1268833-77-7 2-(5,6-dihydro-4H-1,3-oxazin-2-yl)-4-methoxyphenol 

Relevant academic research and scientific papers

Lewis Acid-Mediated Cyanation of Phenols Using N-Cyano-N-phenyl-p-toluenesulfonamide

Lewis acid-mediated cyanation of phenol derivatives with N-cyano-N-phenyl-p-toluenesulfonamide (NCTS) has been developed. The reaction proceeded efficiently with high regioselectivity to produce aromatic nitriles in moderate to excellent yields, which provides a direct and practical access to valuable products. (Figure presented.).

Chromatography-free entry to substituted salicylonitriles: Mitsunobu-triggered domino reactions of salicylaldoximes

A mild and efficient one-pot procedure is described to transform salicylaldoximes into salicylonitriles using Mitsunobu chemistry. The reactions proceed through the corresponding 1,2-benzisoxazoles that undergo the Kemp elimination in situ to generate the

Utility of Nitrogen Extrusion of Azido Complexes for the Synthesis of Nitriles, Benzoxazoles, and Benzisoxazoles

The utility of the nitrogen extrusion reaction of azido complexes, generated in situ from the corresponding aldehydes or ketones with TMSN3 in the presence of ZrCl4 or TfOH, has been described. These azido complexes could undergo three different pathways, depending on the substrates. First, azido methanolate complexes or imine diazonium ions could lead to benzisoxazole products via an intramolecular nucleophilic substitution. Second, imine diazonium ions could also undergo either the elimination of proton to provide nitrile products in good to excellent yields or an aryl migration, followed by an intramolecular nucleophilic addition, to give benzoxazole products in good yields.

HCV PROTEASE INHIBITORS

The present invention discloses a compound of general formula (I); A is O, S, CH, NH or NR', when O links with Z3, Z1 is N or CRZ1, Z2 is CRZ2, when Z1 links with O, Z2 is CH, Z3 is C-Ar; Ra, Rb, Rc and Rd independently is H, OH, halogen or -Y1-Rm; A1 is NH or CH2; R1' is alkyl, aryl, cycloalkyl, heterocycloalkyl or heteroaryl; A2 is N, O or linking bond; R1 is hydrogen, or, R1 linking covalently with R3 forms C5-C9 saturated or unsaturated hydrocarbon chain substituted by O or N; R3 is alkyl, cycloalkyl, heterocycloalkyl, alkyl substituted by cycloalky etc; R4 is alkoxy-CO, alkyl-NHCO, (alkyl)2NCO, or formyl substituted by aryl, cycloalkyl, heterocycloalkyl.

HCV Protease Inhibitors

A compound of general formula (I); A is O, S, CH, NH or NR′, when O links with Z3, Z1 is N or CRZ1, Z2 is CRZ2, when Z1 links with O, Z2 is CH, Z3 is C—Ar; Ra, Rb, Rc and Rd independently is H, OH, halogen or —Y1—Rm; A1 is NH or CH2; R1′ is alkyl, aryl, cycloalkyl, heterocycloalkyl or heteroaryl; A2 is N, O or linking bond; R1 is hydrogen, or, R1 linking covalently with R3 forms C5-C9 saturated or unsaturated hydrocarbon chain substituted by O or N; R3 is alkyl, cycloalkyl, heterocycloalkyl, alkyl substituted by cycloalkyl etc; R4 is alkoxy-CO, alkyl-NHCO, (alkyl)2NCO, or formyl substituted by aryl, cycloalkyl, heterocycloalkyl.

Facile one-pot transformation of phenols into o-cyanophenols

The treatment of phenols with paraformaldehyde in the presence of MgCl2 and Et3N in THF at 80 C, followed by reaction with molecular iodine and aq. ammonia at room temperature provided the corresponding o-cyanophenols in moderate to good yields. The present reaction is a one-pot transformation of phenols into o-cyanophenols using much less expensive reagents than are typically used; the reaction is free of both transition-metals and cyanide. The utility of this reaction was highlighted during our preparation of Febuxostat from p-bromophenol.

A catalytic route to ampakines and their derivatives

A catalytic domino reaction that efficiently provides access to an important class of heterocycles, the ampakines, is reported. Our approach is based on the cobalt-catalyzed hydroformylation of dihydrooxazines and allows for the facile synthesis of the pharmaceutically interesting compound CX-614 and related substances.

BENZOFUROPYRIMIDINONES AS PROTEIN KINASE INHIBITORS

A compound according to formula I: or a pharmaceutically acceptable salt thereof; wherein R1, R2, R3a, R3b, R3c and R3d are as defined in the specification, pharmaceutical compositions thereof, and methods of use thereof.

Synthesis and biological evaluation of 2-(3′,4′,5′-trimethoxybenzoyl)-3-N,N-dimethylamino benzo[b]furan derivatives as inhibitors of tubulin polymerization

Molecules that target microtubules have an important role in the treatment of cancer. A new class of inhibitors of tubulin polymerization based on the 2-(3,4,5-trimethoxybenzoyl)-2-dimethylamino-benzo[b]furan molecular skeleton was synthesized and evaluat

CARBAMOYL-TYPE BENZOFURAN DERIVATIVES

The present invention provides a carbamoyl-type benzofuran derivative of the formula [1]: wherein Ring Z is a group of the formula: etc.; A is a single bond, and the like; Y is a cycloalkanediyl group, etc.; R4 and R5 are the same or different and each is an optionally substituted lower alkyl group, etc.; R1 is a halogen atom, etc.; Ring B of the formula: is an optionally substituted benzene ring; and R3 is a hydrogen atom, etc., or a pharmaceutically acceptable salt thereof, which is useful as an FXa inhibitor.