180264-44-2

Upstream product

• 64187-51-5 N-trimethylsilyl(4-methoxy)benzaldimine 
• 97-72-3 2-Methylpropionic anhydride 
• 1468-39-9 Isovaleric anhydride 
• 637-69-4 4-Methoxystyrene 
• 1189-71-5 isocyanate de chlorosulfonyle 
• 269716-26-9 1-chloro-2-(trimethylsilyl)oxy-3-aza-4-p-methoxy-phenyl-1,3-butadiene 
• 123-11-5 4-methoxy-benzaldehyde 
• 5678-45-5 3-amino-3-(4-methoxyphenyl)propionic acid 

Downstream Products

• 1331772-20-3 C₁₀H₁₁NO₂ 
• 1331772-09-8 C₁₄H₁₇NO₃ 
• 1542817-74-2 2-(4-methoxyphenyl)-1-methylazetidine 
• 1542817-09-3 2-(4-methoxy-2-methylphenyl)-1-methylazetidine 
• 1542817-89-9 C₁₂H₁₇NO 
• 1542817-33-3 [5-methoxy-2-(1-methylazetidin-2-yl)phenyl]diphenylmethanol 
• 1542817-34-4 2-(2-chloro-4-methoxyphenyl)-1-methylazetidine 

Relevant academic research and scientific papers

Harnessing the ortho-directing ability of the azetidine ring for the regioselective and exhaustive functionalization of arenes

This work demonstrates how the directing ability of the azetidine ring could be useful for regioselective ortho-C-H functionalization of aryl compounds. Robust polar organometallic (lithiated) intermediates are involved in this synthetic strategy. The reagent n-hexyllithium emerged as a safer, yet still effective, basic reagent for the hydrogen/lithium permutation relative to the widely used reagent nBuLi. Two different reaction protocols were discovered for regioselective lithiation at the ortho positions adjacent to the azetidine ring, which served as a toolbox when other competing directing groups were installed on the aromatic ring. The coordinating ability of the azetidine nitrogen atom, as well as the involvement of dynamic phenomena related to the preferential conformations of 2-arylazetidine derivatives, were recognized to be responsible for the observed reactivity and regioselectivity. A site-selective functionalization of the aromatic ring was achieved for aryl azetidines with either coordinatively competent groups (e.g. methoxy) or inductively electron-withdrawing substituents (e.g. chlorine and fluorine). By fine-tuning the reaction conditions, regioselective introduction of several substituents on the aromatic ring could be realized. Several substitution patterns were accomplished, which included 1,2,3-trisubstitution, 1,2,3,4-tetrasubstitution, and 1,2,3,4,5-pentasubstitution, up to the exhaustive substitution of the aromatic ring.

Catalytic, enantioselective N-acylation of lactams and thiolactams using amidine-based catalysts

In contrast to alcohols and amines, racemic lactams and thiolactams cannot be resolved directly via enzymatic acylation or classical resolution. Asymmetric N-acylation promoted by amidine-based catalysts, particularly Cl-PIQ 2 and BTM 3, provides a convenient method for the kinetic resolution of these valuable compounds and often achieves excellent levels of enantioselectivity in this process. Density functional theory calculations indicate that the reaction occurs via N-acylation of the lactim tautomer and that cation-π interactions play a key role in the chiral recognition of lactam substrates.

Kinetic resolution of β-lactams via enantioselective N-acylation

Enantioselective N-acylation of 4-aryl-β-lactams in the presence of acyl transfer catalyst Cl-PIQ provides an effective method for their non-enzymatic kinetic resolution.

Use of 2,2′-dibenzothiazolyl disulfide-triphenylphosphine and Lawesson's Reagent in the cyclization of β-amino acids

The disulfide reagents 2,2′-dithiobisbenzothiazole (MBTS) and 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide (Lawesson's Reagent, LR) mediate the cyclization of β-amino acids with remarkable product yields. Compared to other cyclodehydrating agents, these have been found to be superior in terms of their cost, making them industrially viable. The advantageous properties of MBTS and LR make them useful and unique additions to the arsenal of cyclodehydrating agents.

(Chloromethylene)dimethylammonium chloride: A highly efficient reagent for the synthesis of β-lactams from β-amino acids

(Chloromethylene)dimethylammonium chloride 1, is a unique reagent that conveniently and efficiently mediates the amide bond formation in β-lactams via cyclodehydration of β-amino acids leading to β-lactam formation. The process involves the formation of a highly reactive activated ester of a β-amino acid which gets cyclised to the corresponding β-lactam in excellent yield. The reaction proceeds smoothly and cleanly as the by-products formed are the water soluble-dimethyl formamide and triethylamine hydrochloride.

A trans-stereoselective synthesis of 3-halo-4-alkyl(aryl)-NH-azetidin-2-ones

Conrotatory ring closure of 1-halo-3-aza-4-alkyl-1,3-dienes in refluxing toluene gives rise to 3-halo-4-aryl-2-azetidinones in satisfactory yields. Dehalogenation of the resulting β-lactams by tris(trimethylsilyl)silane furnished 3-unsubstituted azetidino