7699-18-5

Usage

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 25, p. 1279, 1988 DOI: 10.1002/jhet.5570250501Tetrahedron Letters, 30, p. 715, 1989 DOI: 10.1016/S0040-4039(01)80290-2

InChI:InChI:1S/C9H9NO2/c1-12-7-2-3-8-6(4-7)5-9(11)10-8/h2-4H,5H2,1H3,(H,10,11)

Upstream product

• 65816-14-0 1-methoxyindolin-2-one 
• 138344-12-4 (2-tert-Butoxycarbonylamino-5-methoxy-phenyl)-acetic acid 
• 1006-94-6 5-methoxylindole 
• 3416-18-0 5-hydroxyoxindole 
• 77-78-1 dimethyl sulfate 
• 102-50-1 2-methyl-4-methoxyaniline 
• 39755-95-8 5-methoxyisatine 
• 59-48-3 2-oxoindole 
• 27387-22-0 2-(2-bromo-5-methoxyphenyl)acetamide 
• 27387-23-1 5-methoxy-2-bromophenylacetonitrile 
• 1581760-83-9 5'-methoxy-3,3-dimethyl-2,3,4,5,10,11-hexahydrospiro[1H-dibenzo-[b,e][1,4]diazepine-11,3'-2H-indole]-1,2'-dione 
• 638563-46-9 C₉H₉N₃O₂ 
• 6335-41-7 2-hydroxyimino-N-(4-methoxyphenyl)acetamide 
• 51-66-1 4-methoxyacetanilide 

Downstream Products

• 141946-37-4 5-Methoxy-3-[1-pyridin-2-yl-meth-(E)-ylidene]-1,3-dihydro-indol-2-one 
• 128564-80-7 5-Methoxy-3-[1-pyridin-4-yl-meth-(Z)-ylidene]-1,3-dihydro-indol-2-one 
• 141946-38-5 5-Methoxy-3-[1-pyridin-3-yl-meth-(E)-ylidene]-1,3-dihydro-indol-2-one 
• 141946-38-5 5-Methoxy-3-[1-pyridin-3-yl-meth-(Z)-ylidene]-1,3-dihydro-indol-2-one 
• 141946-39-6 5-Methoxy-3-[1-(6-methyl-pyridin-2-yl)-meth-(E)-ylidene]-1,3-dihydro-indol-2-one 
• 52508-88-0 5-methoxy-2-oxo-2,3-dihydro-indole-3-carbaldehyde 
• 222533-48-4 5-methoxy-3-(3-methylbut-2-enyl)-2-oxindole 
• 374898-41-6 tert-butyl 5-methoxy-2-oxoindoline-1-carboxylate 

Relevant academic research and scientific papers

A Unified Catalytic Asymmetric (4+1) and (5+1) Annulation Strategy to Access Chiral Spirooxindole-Fused Oxacycles

A unified catalytic asymmetric (N+1) (N=4, 5) annulation reaction of oxindoles with bifunctional peroxides has been achieved in the presence of a chiral phase-transfer catalyst (PTC). This general strategy utilizes peroxides as unique bielectrophilic four- or five-atom synthons to participate in the C?C and the subsequent umpolung C?O bond-forming reactions with one-carbon unit nucleophiles, thus providing a distinct method to access the valuable chiral spirooxindole-tetrahydrofurans and -tetrahydropyrans with good yields and high enantioselectivities under mild conditions. DFT calculations were performed to rationalize the origin of high enantioselectivity. The gram-scale syntheses and synthetic utility of the resultant products were also demonstrated.

A novel methodology for the efficient synthesis of 3-monohalooxindoles by acidolysis of 3-phosphate-substituted oxindoles with haloid acids

A novel method for the synthesis of 3-monohalooxindoles by acidolysis of isatin-derived 3-phosphate-substituted oxindoles with haloid acids was developed. This synthetic strategy involved the preparation of 3-phosphate-substituted oxindole intermediates and SN1 reactions with haloid acids. This new procedure features mild reaction conditions, simple operation, good yield, readily available and inexpensive starting materials, and gram-scalability.

Synthesis of Lactams via Ir-Catalyzed C-H Amidation Involving Ir-Nitrene Intermediates

x-membered lactams were synthesized via either an amidation of sp3 C-H bonds or an electrophilic substitution of arenes via Ir-nitrene intermediates. With the employment of a readily available iridium catalyst in dichloromethane or hexafluoro-2-propanol, a wide range of lactams were synthesized in good to excellent yields with high selectivity.

METHOD FOR PRODUCING LACTAM COMPOUND, AND LACTAM COMPOUND PRODUCED THEREBY

The present invention relates to a method for producing a lactam compound from dioxazolone in the presence of a catalyst having a particular ligand, and to a lactam compound produced thereby, and can produce a lactam compound with excellent selectivity and an excellent yield by using the combination of a starting material having a particular functional group and a particular catalyst having a particular ligand.

Synthesis of Functionalized Indolines and Dihydrobenzofurans by Iron and Copper Catalyzed Aryl C-N and C-O Bond Formation

A simple and effective one-pot, two-step intramolecular aryl C-N and C-O bond forming process for the preparation of a wide range of benzo-fused heterocyclic scaffolds using iron and copper catalysis is described. Activated aryl rings were subjected to a highly regioselective, iron(III) triflimide-catalyzed iodination, followed by a copper(I)-catalyzed intramolecular N-or O-arylation step leading to indolines, dihydrobenzofurans, and six-membered analogues. The general applicability and functional group tolerance of this method were exemplified by the total synthesis of the neolignan natural product, (+)-obtusafuran. DFT calculations using Fukui functions were also performed, providing a molecular orbital rationale for the highly regioselective arene iodination process.

Synthesis and Reactivity of 3,3-Diazidooxindoles

The synthesis of previously unknown 3,3-diazidooxindoles as synthetically useful derivatives of isatins was accomplished through the direct oxidative diazidation of 2-oxindoles. The method yielded the diazido compounds from the starting oxindoles under mild and simple conditions with NaN3 and iodine, in good yields. The notable reactivity of this new class of compounds toward primary and secondary nucleophilic amines is also described, which gives access to either 4-imino-3,4-dihydroquinazolin-2(1H)-one derivatives or cyanophenylureas.

Revisiting Arene C(sp2)?H Amidation by Intramolecular Transfer of Iridium Nitrenoids: Evidence for a Spirocyclization Pathway

Two mechanistic pathways, that is, electrocyclization and electrophilic aromatic substitution, are operative in most intramolecular C?H amination reactions proceeding by metal nitrenoid catalysis. Reported here is an alternative mechanistic scaffold leading to benzofused δ-lactams selectively. Integrated experimental and computational analysis revealed that the reaction proceeds by a key spirocyclization step followed by a skeletal rearrangement. Based on this mechanistic insight, a new synthetic route to spirolactams has been developed.

Selective formation of γ-lactams via C-H amidation enabled by tailored iridium catalysts

Intramolecular insertion of met al nitrenes into carbon-hydrogen bonds to form γ-lactam rings has traditionally been hindered by competing isocyanate formation. We report the application of theory and mechanism studies to optimize a class of pentamethylcyclopentadienyl iridium(III) catalysts for suppression of this competing pathway. Modulation of the stereoelectronic properties of the auxiliary bidentate ligands to be more electron-donating was suggested by density functional theory calculations to lower the C-H insertion barrier favoring the desired reaction. These catalysts transform a wide range of 1,4,2-dioxazol-5-ones, carbonylnitrene precursors easily accessible from carboxylic acids, into the corresponding γ-lactams via sp3 and sp2 C-H amidation with exceptional selectivity. The power of this method was further demonstrated by the successful late-stage functionalization of amino acid derivatives and other bioactive molecules.

Synthesis of novel 3-(benzothiazol-2-ylmethylene)indolin-2-ones

A mild method for the synthesis of 3-(benzothiazol-2-ylmethylene)indolin-2-ones via the aldol condensation of substituted indolin-2-ones and benzothiazole-2-carbaldehyde is described. This new procedure has significant advantages, such as mild conditions, high yields and simple work-up.

Palladium-Catalyzed C-H Activation and Cyclization of Anilides with 2-Iodoacetates and 2-Iodobenzoates: An Efficient Method toward Oxindoles and Phenanthridones

A concise approach to the synthesis of oxindoles and phenanthridones from anilides is described. In the presence of catalytic amount of Pd(OAc)2, 2-iodoacetates and 2-iodobenzoates can be used to functionalize ortho C-H bond of anilides, which subsequently undergo intramolecular cyclization to give the products. A possible reaction mechanism that involves a PdII/PdIV catalytic cycle is proposed with the support of detailed mechanistic studies.