42180-82-5

Usage

InChI:InChI=1/C9H7ClO/c1-6-4-7-5-8(10)2-3-9(7)11-6/h2-5H,1H3

Upstream product

• 102806-77-9 Acetic acid 2-bromomethyl-4-chloro-phenyl ester 
• 121045-30-5 4-chloro-2-<2-hydroxy-1-(isopropylthio)propyl>phenol 
• 197314-83-3 Ethyl 2-methyl-3-(2-allyloxy-5-chlorophenyl)propenoate 
• 53299-55-1 1-(4-chlorophenoxy)-2-chloro-2-propene 
• 90798-13-3 2-(4-CHLORO-2-FORMYLPHENOXY)PROPANOIC ACID 
• 13997-73-4 2-allyl-4-chlorophenol 
• 95186-48-4 4-chloro-2-<2',2'-dibromo ethenyl>-phenol 
• 1191415-19-6 2-bromo-5-chloro-benzo[b]furan 
• 75-24-1 trimethylaluminum 
• 71643-66-8 4-chloro-2-iodo phenol 
• 1240289-04-6 methyl 2-(2-bromo-4-chlorophenoxy)propanoate 
• 695-96-5 2-bromo-4-chlorophenol 
• 200625-39-4 C₁₄H₁₃ClN₂O₃S 

Relevant academic research and scientific papers

Highly Efficient Synthesis of 2-Substituted Benzo[ b ]furan Derivatives from the Cross-Coupling Reactions of 2-Halobenzo[ b ]furans with Organoalane Reagents

A highly efficient and simple route for the synthesis of 2-substituted benzo[ b ]furans has been developed by palladium-catalyzed cross-coupling reaction of 2-halobenzo[ b ]furans with aryl, alkynyl, and alkylaluminum reagents. Various 2-aryl-, 2-alkynyl-, and 2-alkyl-substituted benzo[ b ]furan derivatives can be obtained in 23-97% isolated yields using 2-3 mol% PdCl 2/4-6 mol% XantPhos as the catalyst under mild reaction conditions. The aryls bearing electron-donating or electron-withdrawing groups in 2-halobenzo[ b ]furans gave products in 40-97% isolated yields. In addition, aluminum reagents containing thienyl, furanyl, trimethylsilanyl, and benzyl groups worked efficiently with 2-halobenzo[ b ]furans as well, and three bioactive molecules with 2-substituted benzo[ b ]furan skeleton were synthesized. Furthermore, the broad substrates scope and the typical maintenance of vigorous efficiency on gram scale make this protocol a potentially practical method to synthesize 2-substituted benzo[ b ]furan derivatives. On the basis of the experimental results, a possible catalytic cycle has been proposed.

Discovery of orthogonal synthesis using artificial intelligence: Pd(OAc)2-catalyzed one-pot synthesis of benzofuran and bicyclo[3.3.1]nonane scaffolds

A synthetic route for the common intermediate, methyl 2-formylbenzofuran-7-carboxylate (7a), to efficiently assemble three bioactive benzofurans 4–6 was explored using the artificial intelligence system SYNSUP. Among the routes proposed by SYNSUP, we investigated a three-step synthesis of 7a using methyl 4-ally-3-oxohept-6-enoate (10). A new catalytic reaction was found in which 7a was directly obtained from 10 in a single step with a yield of 24percent. It was found that this chemical yield could be increased to 74percent when methyl 3-allyl-2-hydroxybenzoate (9a), an intermediate of the above one-pot transformation, was subjected to the catalytic process. In addition, in this catalytic process, 8a (76percent) and 11 (77percent) were each selectively synthesized from 10 by changing only the solvent. Therefore, we created a novel orthogonal synthesis of methyl 2-methylbenzofuran-7-carboxylate (8a) and methyl 9-oxobicyclo[3.3.1]nona-3,6-diene-1-carboxylate (11). Finally, the total syntheses of bioactive benzofurans 4–6 were completed smoothly using 7a and 8a.

Pd-catalyzed intramolecular Heck reaction for the synthesis of 2-methylbenzofurans

A new strategy for the synthesis of 2-Methylbenzofurans via the intramolecular Heck reaction has been developed. This efficient palladium-catalyzed system showed good catalytic activity. Various substituted 2-methylbenzofurans could be afforded in good to excellent yields.

Direct Synthesis of 2-Methylbenzofurans from Calcium Carbide and Salicylaldehyde p -Tosylhydrazones

A new methodology for the construction of methyl-substituted benzofuran rings from the reactions of calcium carbide with salicylaldehyde p-tosylhydrazones/2-hydroxyacetophenone p-tosylhydrazones is described. Various 2-methylbenzofurans and 2,3-dimethylbenzofurans could be obtained in satisfactory yield by using a cuprous chloride catalyst. The advantages of this protocol include the use of a readily available and easy-to-handle acetylene source and simple workup procedure.

An efficient solid-phase synthesis of substituted benzofuran using selenium-bound resin

A very efficient solid-phase synthesis of substituted benzofuran using polymer-supported selenium resin is described. The advantages of the new method are good yields, high purity, straightforward operations, broad range and high diversity of products, lack of odor, and good stability of the resins. The easy work-up procedure makes the method suitable for building parallel libraries.

Preparation of 2-, 3-, 4- and 7-(2-alkylcarbamoyl-1-alkylvinyl)benzo[b] furans and their BLT1 and/or BLT2 inhibitory activities

Several 2-alkylcarbamoyl-1-alkylvinylbenzo[b]furans were designed to find a selective leukotriene B4 (LTB4) receptor antagonist. 2-(2-Alkylcarbamoyl-1-alkylvinyl)benzo[b]furans having a substituent group at the 3-position, 4-(2-alkylcarbamoyl-1-methylvinyl)benzo[b]furans having a substituent group at the 3-position, and 7-(2-alkylcarbamoyl-1-methylvinyl) benzo[b]furans and 3-(2-alkylcarbamoyl-1-alkylvinyl)benzo[b]furans were prepared and evaluated for LTB4 receptor (BLT1 and BLT 2) inhibitory activities. (E)-3-Amino-4-[2-[2-(3,4-dimethoxyphenyl) ethylcarbamoyl]-1-methylvinyl]benzo[b]furan ((E)-17c) showed potent and selective inhibitory activity for BLT2. On the other hand, (E)-7-(2-diethylcarbamoyl-1-methylvinyl)benzo[b]furan ((E)-27a) showed potent inhibitory activity for both BLT1 and BLT2. This journal is The Royal Society of Chemistry.

An elegant and unprecedented approach to 2-methylbenzofurans

An effective route for the synthesis of a variety of 2-methylbenzofurans is reported via DBU catalyzed dehydroiodination of easily accessible 2-iodomethyl-2,3-dihydrobenzofurans. The latter could be easily obtained by water mediated iodocyclization of allyl phenols.

Hypoglycemic imidazoline compounds

This invention relates to certain novel imidazoline compounds and analogues thereof, to their use for the treatment of diabetes, diabetic complications, metabolic disorders, or related diseases where impaired glucose disposal is present, to pharmaceutical compositions comprising them, and to processes for their preparation.

Hypoglycemic imidazoline compounds

This invention relates to certain novel imidazoline compounds and analogues thereof, to their use for the treatment of diabetes, diabetic complications, metabolic disorders, or related diseases where impaired glucose disposal is present, to pharmaceutical compositions comprising them, and to processes for their preparation. The compounds have the following formula: whereinX is -O-, -S-, or -NR5-;R5 is hydrogen, C1-8 alkyl, or an amino protecting group;R1, R1', R2, and R3 are independently hydrogen or C1-8 alkyl;R1 and R2 optionally together form a bond and R1' and R3 are independently hydrogen or C1-8 alkyl;R1 and R2 optionally combine together with the carbon atoms to which they are attached form a C3-7 carbocyclic ring and R1' and R3 are independently hydrogen or C1-8 alkyl;R1 and R1' together with the carbon atom to which they are attached optionally combine to form a C3-7 spirocarbocyclic ring and R2 and R3 are independently hydrogen or C1-8 alkyl;R2 and R3 together with the carbon atom to which they are attached optionally combine to form a C3.7 spirocarbocyclic and R1 and R1' are independently hydrogen or C1-8 alkyl;n is 0, 1, or 2;m is 1 or2; 2;m' is 0, 1, or 2;q' is 0,1,2,3,4, or 5;R4 isY is -O-, -S-, or -NR8-;Y' is -O- or -S-;R6 and R7 are independently hydrogen, C1-8 alkyl, C3-7 cycloalkyl, C1-8 alkoxy, C1-8 alkylthio, halo C1-8 alkylthio, C1-8 alkylsulfinyl, C1-8 alkylsulfonyl. C3-7 cycloalkoxy, aryl-C1-8 alkoxy, halo, halo-C1-8 alkyl, halo-C1-8 alkoxy, nitro, -NR10R11, -CONR10R11, aryl C1-8 alkyl, optionally substituted heterocyclyl, optionally substituted phenyl, optionally substituted naphthyl, optionally halo substituted acylamino, cyano, hydroxy, COR12, halo C1-8 alkylsulfinyl, or halo C1-8 alkylsulfonyl, or alkoxyalkyl of the formulaCH3(CH2)p-O-(CH2)q-O-; wherep is 0, 1, 2, 3, or 4; andq is 1, 2, 3, 4, or 5;R12 is C1-8 alkyl or optionally substituted phenyl;R8 is hydrogen, C1-8 alkyl, halo-C1-8 alkyl, optionally substituted phenyl, optionally substituted heterocyclyl, COO C1-8 alkyl, optionally substituted COaryl, COC1-8 alkyl, SO2C1-8 alkyl, optionally substituted SO2 aryl, optionally substituted phenyl-C1-8 alkyl, CH3(CH2)p-O-(CH2)q-O-;R9 is hydrogen, halo, C1-8 alkyl, halo C1-8 alkyl, C1-8 alkylthio, halo C1-8 alkylthio, C3-7 cycloalkylthio, optionally substituted arylthio or heteroarylthio, C1-8 alkoxy, C3-8 cycloalkoxy, optionally substituted aryloxy, optionally substituted heteroaryloxy, or optionally substituted aryl or heteroaryl, C3-7 cycloalkyl, halo C3-7 cycloalkyl, C3-7 cycloalkenyl, cyano, COOR10,CONR10R11 or NR10R11,C2-6 alkenyl, optionally substituted heterocyclyl, optionally substituted aryl C1-8 alkyl, optionally substituted heteroaryl C1-8 alkyl in which the alkyl group can be substituted by hydroxy, or C1-8 alkyl substituted by hydroxy,R10 and R11 are independently hydrogen, C1-8 alkyl, optionally substituted aryl C1-8 alkyl, optionally substituted phenyl, or R10 and R11 together with the nitrogen atom to which they are attached may combine to form a ring with up to six carbon atoms which optionally may be substituted with up to two C1-8 alkyl groups or one carbon atom may be replaced by oxygen or sulfur;R14 and R16 are independently hydrogen, halo, C1-8 alkyl, C3-7 cycloalkyl, C3-7 cycloalkoxy, C3-7 cycloalkylC1-8 alkoxy, halo-C1-8 alkyl, halo-C1-8 alkoxy, C1-8 alkoxy, carbo(C1-8)alkoxy, optionally substituted aryl, or optionally substituted heteroaryl;R15 and R17 are independently hydrogen, halo, C1-8 alkoxy, C3-7-cycloalkyl, C3-7 cycloalkylC1-8 alkoxy, C1-8 alkyl, C3-7 cycloalkoxy, hydroxy, halo C1-8 alkoxy, carbo(C1-8)alkoxy, optionally substituted phenyl, optionally substituted phenyl-C1-8 alkyl, optionally substituted phenyloxy, optionally substituted phenyl-C1-8 alkoxy, (tetrahydropyran-2-yl)methoxy, C1-8 alkyl-S(O)m-, optionally substituted aryl-C1-8 alkyl-S(O)m·-, CH3(CH2)p-Z1-(CH2)q-Z2-, or Z3-(CH2)q'-Z2-;Z1 and Z2 are independently abond, O, S, SO, SO2, sulphoximino, or NR10; andZ3 is hydroxy, protected hydroxy, NR10 R11, protected amino, SH or protected SH; ???provided that when R1, R1', R2 and R3 are all hydrogen; n is 0; R4 is naphthyl; and R14 R15 and R16, or R15, R16 and R17 are all hydrogen, then R17 or R14, respectively, is other than halo, methoxy, or C1-6 alkyl. ???or a pharmaceutically acceptable salt or ester thereof.

Pyridazinone aldose reductase inhibitors

The present invention relates to novel pyridazinone compounds, pharmaceutical compositions comprising those compounds and to methods of using such compounds and compositions to inhibit aldose reductase, lower sorbitol levels and, thus, lower fructose levels, and/or treat or prevent diabetic complications such as diabetic neuropathy, diabetic retinopathy, diabetic nephropathy, diabetic cardiomyopathy, diabetic microangiopathy and diabetic macroangiopathy in mammals. This invention also relates to methods of affording cardioprotection to subjects not suffering from diabetes. This invention also relates to pharmaceutical compositions and kits comprising a combination of an aldose reductase inhibitor (ARI) of this invention and a sorbitol dehydrogenase inhibitor and to methods of using such compositions or kits to treat or prevent the above diabetic complications in mammals. This invention also relates to other combinations with the ARIs of this invention, including combinations with adendsine agonists; NHE-1 inhibitors; glycogen phosphorylase inhibitors; selective serotonin reuptake inhibitors; GABA agonists; antihypertensive agents; 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitors; phosphodiesterase-5 inhibitors; and to glucose lowering agents.