13033-52-8

Upstream product

• 75-31-0 isopropylamine 
• 105-13-5 4-Methoxybenzyl alcohol 
• 123-11-5 4-methoxy-benzaldehyde 
• 70894-74-5 [(4-methoxyphenyl)methyl](propan-2-yl)amine 
• 7464-44-0 4-methoxy-N-(1-methylethyl)benzamide 
• 110079-26-0 C₁₁H₁₆ClNO 

Downstream Products

• 70894-74-5 [(4-methoxyphenyl)methyl](propan-2-yl)amine 
• 62212-22-0 1,2-bis(4-methoxybenzyl)diselane 
• 418765-66-9 3,3-dichloro-1-isopropyl-4-(4-methoxyphenyl)-2-azetidinone 
• 6968-77-0 3-(4-methoxyphenyl)-2-phenylacrylic acid 
• 117617-34-2 (4R,5R)-5-Hydroxymethyl-4-(4-methoxy-phenyl)-2-oxy-4,5-dihydro-isoxazole-3-carboxylic acid methyl ester 
• 418765-76-1 2-[dimethoxy(4-methoxyphenyl)methyl]-1-isopropylaziridine 
• 418765-71-6 3,3-dichloro-1-isopropyl-2-(4-methoxyphenyl)azetidine 

Relevant academic research and scientific papers

A General Way to Construct Arene-Fused Seven-Membered Nitrogen Heterocycles

Imines react with seven-membered cyclic anhydrides (prepared from the corresponding dicarboxylic acids by a recently discovered in-situ cyclodehydration protocol) by the Castagnoli–Cushman reaction pathway to give privileged seven-membered arene-fused nitrogen-heterocyclic compounds with reagent-controlled diversity of the skeleton and peripheral groups.

Novel one-pot synthesis of 3-amino-1-alkenylphophonates by addition of imines to alkynylphosphonate titanium(II) complexes

(Matrix presented) A new method of synthesis of 3-amino-1-alkenylphosphonates is described. It involves the addition of imines to the alkynylphosphonate titanium(II) complexes 2, which are prepared in situ from 1-alkynylphosphonates and Ti(O-i-Pr)4/2 equiv of i-PrMgCl. Compounds 4a-i were obtained regio- and stereoselectivily in high yields.

One-pot synthesis of alternating peptides exploiting a new polymerization technique based on Ugi's 4CC reaction

We developed a one-pot synthetic technique for alternating peptides. Central to this technique is a new, catalyst-free polymerization based on Ugi's 4CC reaction. The treatment of imines with the ambident molecules bearing both an isocyanide and a carboxylic acid afforded alternating peptides.

Kinetics and mechanism of the Pudovik reaction in the azomethine series: I. Addition of dimethyl hydrogen phosphite to N-isopropylbenzalimines

For a series of phenyl-substituted N-isopropylbenzalimines, the effect of substituent on their capability to add dimethyl hydrogen phosphite was studied qualitatively in the condensed phase (DTA) and quantitatively (with determination of the kinetic and activation parameters) in 2-propanol solutions with spectrophotometric monitoring of the reaction. A reaction mechanism was proposed, involving formation of a highly organized four-membered transition state.

Arene diruthenium(II)-mediated synthesis of imines from alcohols and amines under aerobic condition

The utility and selectivity of the newly synthesized dinuclear arene Ru(II) complex were demonstrated towards the synthesis of imines from coupling of alcohols and amines in the aerobic condition. Analytical and various spectral methods have been used to establish the unprecedented formation of the new thiolato-bridged dinuclear ruthenium complex. The molecular structure of the titled complex was evidenced with aid of X-ray crystallographic technique. A wide range of imines were obtained in good-to-excellent yields up to 98% and water as the by-product through an acceptorless dehydrogenative coupling of alcohols with amines. The catalytic reaction operated a concise atom economical without any oxidant with 1 mol% of the catalyst load. Further, the role of base, solvent and catalyst loading of the coupling reaction has been investigated. A plausible mechanism has been described and was found to proceed via the formation of an aldehyde intermediate. Short synthesis of antibacterial drug N-(salicylidene)-2-hydroxyaniline illustrated the utility of the present protocol.

Nucleophilic Imines and Electrophilic o-Quinone Methides, a Three-Component Assembly of Assorted 3,4-Dihydro-2 H-1,3-benzoxazines

A one-pot method for joining three separate components leading to an assortment of N-substituted 3,4-dihydro-2H-1,3-benzoxazines is described. The method involves the addition of a Grignard reagent to an o-OBoc salicylaldehyde in the presence of an imine. With a variety of components, 15 examples are presented, including the diastereoselective incorporation of chiral imines.

Cobalt-Catalyzed α-Arylation of Substituted α-Halogeno β-Lactams

The treatment of 3-bromo β-lactams by an aryl Grignard, in the presence of CoCl2 (2 mol %) and TMEDA (2 mol %) in THF, produces 3-aryl β-lactams in good yields and excellent diastereoselectivity.

Microwave-assisted diastereoselective two-step three-component synthesis for rapid access to drug-like libraries of substituted 3-amino-β-lactams

Large, diverse compound libraries are an essential requisite in target-based drug development. In this work, a robust microwave-assisted synthesis for the diastereoselective generation of 3-saccharinyl-trans-β-lactams is reported. The method is optimised

Mixed carboxylic-sulfonic anhydride in reaction with imines: A straightforward route to water-soluble β-lactams via a Staudinger-type reaction

The first example of employing a mixed carboxylic-sulfonic anhydride in reaction with imines is reported. Unlike its well-studied isostere homophthalic anhydride, benzo[c][1,2]oxathiin-3(4H)-one 1,1-dioxide gave no product of a formal [4 + 2] cycloaddition and only followed an alternative reaction pathway toward β-lactams, presumably, via a formal [2 + 2] cycloaddition (a Staudinger-type reaction). Optimized reaction conditions involve the use of triethylamine as a base promoter, which also allows isolating the product β-lactam benzene sulfonic acids as respective triethylammonium salts by conventional column chromatography. The reaction shows some preference to trans-isomer formation; pure diastereomers can be isolated in some cases.

Development of a metal-free amine oxidation method utilizing DEAD chemistry

Herein, we examine the oxidative abilities of azodicarboxylates for the conversion of amines to imines. This method provides access to synthetically useful imine intermediates including β-carbolines, quinazolines and N-heterocyclic carbene precursors. The ability to recover spent azodicarboxylate for regeneration and further use underscores the applicability and appeal of this protocol.