366453-22-7

Usage

Uses

Used in Organic Chemistry:
1H-Isoindol-1-one,2,3-dihydro-4-methoxy-(9CI) is used as a building block for the synthesis of various organic compounds, leveraging its versatile reactivity to form a wide range of substances with different applications.
Used in Pharmaceutical Industry:
1H-Isoindol-1-one,2,3-dihydro-4-methoxy-(9CI) is used as a key intermediate in the development of bioactive molecules, contributing to the creation of pharmaceuticals with potential therapeutic effects. Its chemical structure and properties make it a valuable component in the production of drugs with diverse applications in medicine.

Upstream product

• 71887-28-0 methyl 2-(bromomethyl)-3-methoxybenzoate 
• 55289-06-0 3-methoxy-2-methylbenzoic acid 
• 6850-57-3 2-methoxybenzylamine 
• 201230-82-2 carbon monoxide 
• 42981-93-1 3-methoxy-2-methylbenzoic acid methyl ester 

Downstream Products

• 366453-21-6 4-hydroxyisoindolin-1-one 
• 1263311-24-5 C₁₉H₁₉NO₄ 

Relevant academic research and scientific papers

Ruthenium-Catalyzed Carbonylation of Oxalyl Amide-Protected Benzylamines with Isocyanate as the Carbonyl Source

An efficient synthesis of isoindolin-1-ones from oxalyl amide-protected benzylamines, through ruthenium-catalyzed intramolecular C(sp2)-H carbonylation, has been developed. Variously substituted benzylamines could be well tolerated in this new protocol, affording the corresponding products in moderate to excellent yields. This approach constitutes the first example of Ru(II)-catalyzed C(sp2)-H carbonylation with isocyanate as a novel commercially available carbonyl source.

Pd-Catalyzed C(sp2)?H Alkoxycarbonylation of Phenethyl- and Benzylamines with Chloroformates as CO Surrogates

The site-selective functionalization of C?H bonds within a complex molecule remains a challenging task of capital synthetic importance. Herein, an unprecedented Pd-catalyzed C(sp2)?H alkoxycarbonylation of phenylalanine derivatives and other amines featuring picolinamide as the directing group (DG) is reported. This oxidative coupling is distinguished by its scalability, operational simplicity, and avoids the use of toxic carbon monoxide as the C1 source. Remarkably, the easy cleavage of the DG enables the efficient assembly of isoindolinone compounds. Density Functional Theory calculations support a PdII/PdIV catalytic cycle.

Palladium-Catalyzed Direct C-H Carbonylation of Free Primary Benzylamines: A Synthesis of Benzolactams

A protocol for palladium-catalyzed C-H carbonylation of readily available free primary benzylamines using NH2 as the chelating group under an atmospheric pressure of CO has been achieved, providing a general, atom- and step-economic approach to

Synthesis and antibacterial activity of pleuromutilin derivatives with novel C(14) side chain

In order to find novel antibacterial agents with superior antibacterial activity and overcoming multidrug resistance, a series of pleuromutilin derivatives with novel C(14) side chain were synthesized and evaluated for their in vitro antibacterial activit

Design, synthesis, and structure-activity relationship studies of conformationally restricted mutilin 14-carbamates

We report herein the design, synthesis, and structure-activity relationship studies of conformationally restricted mutilin 14-carbamates based on the structure of SB-222734. The antibacterial activities of these newly synthesized compounds were also evaluated and compared with linezolid and retapamulin. Results showed that most of the target compounds exhibit good potency in inhibiting the growth of Gram-positive bacteria including Methicillin- susceptible Staphylococcus aureus MSSA (MIC: 0.0625-2 μg/mL), Methicillin-resistant S. aureus MRSA (MIC: 0.0625-2 μg/mL), Methicillin-susceptible Staphylococcus epidermidis MSSE (MIC: 0.0625-2 μg/mL), Methicillin-resistant S. epidermidis MRSE (MIC: 0.0625-2 μg/mL), and Streptococcus pneumonia (MIC: 0.0625-4 μg/mL). In particular, three remarkable compounds of this series (12l, 12m, and 21l) exhibited comparable in vitro antibacterial profiles to that of retapamulin.

A simple and convenient one-pot synthesis of substituted isoindolin-1-ones via lithiation, substitution and cyclization of N'-benzyl-N,N-dimethylureas

Lithiation of N'-benzyl-N,N-dimethylurea and its substituted derivatives with t-BuLi (3.3 equiv) in anhydrous THF at 0 °C followed by reaction with various electrophiles afforded a range of 3-substituted isoindolin-1-ones in high yields.

One-pot synthesis of substituted isoindolin-1-ones via lithiation and substitution of N′-benzyl-N,N-dimethylureas

Lithiation of various N′-benzyl-N,N-dimethylureas with t-BuLi (3.3 mole equivalents) in anhydrous THF at 0 °C followed by reactions with various electrophiles afforded the corresponding 3-substituted isoindolin-1-ones in high yields.

HETEROCYCLIC AMIDE COMPOUNDS AS PROTEIN KINASE INHIBITORS

The present invention related to novel heterocyclic amide compounds of Formula 1: as disclosed herein or a pharmaceutically accept able salt, solvate, ester, prodrug or stereoisomer thereof. Also disclosedare compositions comprising said compounds, and methods for using said compounds for treating or preventing a proliferative disease, an anti-proliferative disorder, inflammation, arthritis, a neurological or neurodenerative disease, a cardiovascular disease, alopecia, a neuronal disease, an ischemic injury, a viral disease or a fungal disease

NON-NUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITORS

Compounds represented by formula (1), wherein R1 is H, halogen, (C1-4)alkyl, O(C1-4)alkyl, and haloalkyl; R2 is H or methyl; R3 is H or (C1-4)alkyl; R4 is H or (C1-4)a

Non-nucleoside reverse transcriptase inhibitors

Compounds represented by formula I: wherein R1 is H, halogen, (C1-4)alkyl, O(C1-4)alkyl, and haloalkyl; R2 is H or (C1-4)alkyl; R3 is H or (C1-4)alkyl; R4 is (C1-4)alkyl, (C1-4)alkyl(C3-7)cycloalkyl, or (C3-7)cycloalkyl; and Q is a fused phenyl-5 or 6-membered saturated heterocycle having one to two heteroatoms selected from O and N, said Q being optionally substituted with hydroxy, or (C1-4)alkyl which in turn maybe optionally substituted with pyridinyl-N-oxide or C(O)OR wherein R is H or (C1-4)alkyl; or a salt thereof. The compounds have inhibitory activity against Wild Type, and single and double mutants strains, of HIV.