4640-77-1

Upstream product

• 109-73-9 N-butylamine 
• 292638-85-8 acrylic acid methyl ester 

Downstream Products

• 1028560-07-7 C₂₉H₄₁N₃O₅S 
• 19522-69-1 N-butylethylenediamine 
• 1431557-77-5 C₁₇H₂₃N₃O₂ 
• 1431558-10-9 C₂₄H₃₁N₃O₃ 
• 1431558-09-6 C₂₁H₃₃N₃O₃ 
• 1431558-08-5 C₁₉H₂₉N₃O₃ 
• 1431558-07-4 C₁₈H₂₇N₃O₃ 
• 1431558-03-0 C₂₉H₃₉N₃O₅ 
• 1431558-02-9 C₂₆H₄₁N₃O₅ 
• 1431558-01-8 C₂₄H₃₇N₃O₅ 
• 1431558-00-7 C₂₃H₃₅N₃O₅ 
• 1431557-95-7 C₂₂H₃₃N₃O₅ 
• 1431557-91-3 C₁₇H₂₅N₃O₃ 
• 1431557-88-8 C₁₉H₂₉NO₇S 

Relevant academic research and scientific papers

Polymer coated magnetically separable organocatalyst for C[sbnd]N bond formation via aza-Michael addition

A polyacrylamide coated magnetite (PAM@MNP) catalyst was synthesized by following a two step approach involving the reaction of magnetite (Fe3O4) particles with coupling agent 3-(trimethoxysilyl)propyl methacrylate followed by grafting of acrylamide and subsequent polymerization via surface initiated radical polymerization technique. The synthesized organocatalyst was used for a one-pot aza-Michael addition reaction of amines with electron deficient alkenes to give β-amino carbonyls. The magnetic properties of the synthesized organocatalyst provide it a facile recovery by external magnet which eliminates the problems arising during catalyst separation by conventional filtration.

Lipase immobilization on hyroxypropyl methyl cellulose support and its applications for chemo-selective synthesis of β-amino ester compounds

The present study carried out the synthesis of β-amino ester compounds using lipase immobilized on hyroxypropyl methyl cellulose (HMC) support. Initially various lipases (biocatalysts) from different origin were immobilized and subsequently screened to obtain the robust biocatalyst. The lipase Pseudomonas fluorescence (PFL) immobilized on HMC was displayed highest lipase activity, protein content and retention of activity. The physical and biochemical characterization verified immobilization of lipase PFL on the HMC support. This immobilized biocatalyst HMC:PFL (3.5:1) was successfully applied for the practical biocatalytic applications to synthesize variety of β-amino esters. Various eight reaction parameters were optimized in details to achieve the maximum yield and chemo-selectively. The developed biocatalytic protocol was successfully applied to synthesize different industrially important β-amino esters compounds (21 substrates) with an excellent yield (>90%) and remarkable chemo selectivity (>94%). Interestingly, the immobilized HMC:PFL lipase showed 2.1–2.5 folds higher bio-catalytic activity and five times recyclability as compared to the free PFL. The plausible mechanism for lipase catalyzed synthesis of β-amino ester compounds was also proposed.

Aza-Michael reaction: Selective mono- versus bis-addition under environmentally-friendly conditions

Aza-Michael reactions between primary amines and methyl propenoate have been investigated under environmentally-friendly solventless heterogeneous catalysis in order to obtain the mono- or the bis-adduct. The reaction conditions can be altered so as to maximise the yields of the required product with high selectivity.

Carboxylate-assisted formation of alkylcarbonate species from co 2 and tetramethylammonium salts with a β-amino acid anion

Tetramethylammonium-based molten salts bearing a β-amino acid anion (TMAAs) are synthesized through Michael addition reactions of amines with methyl acrylate followed by hydrolysis and subsequent neutralization by using aqueous tetramethylammonium hydroxide. The CO2 capture performances of the TMAAs are evaluated and are shown to interact with CO2 in a 1:1 mode in both water and alcohol. FTIR and 13C NMR spectroscopic studies on the interactions of TMAAs with CO2 indicate that the type of CO 2 adduct varies with the solvent used. When water is used as the solvent, a bicarbonate species is produced, whereas hydroxyethylcarbonate and methylcarbonate species are generated in ethylene glycol and methanol, respectively. Computational calculations show that the carboxylate groups of TMAAs contribute towards the formation and stabilization of 1:1 CO2 adducts through hydrogen bonding interactions with the hydrogen atoms of the amino groups.

Synthesis of tetrahydropyrazolo[1,5- C ]pyrimidine-2,7(1 H,3 H)-diones

A series of tetrahydropyrazolo[1,5-c]pyrimidine-2,7(1H,3H)-diones 3a-h as the first representatives of the so far unexplored saturated heterocyclic system have been synthesized, formally in 12 steps from methyl acrylate (4). The synthesis comprises a four-step preparation of methyl N-Cbz-5-alkylamino-3- oxopentanoates 9a-c, their three-step transformation into 5-{2-[(alkyl) (benzyloxycarbonyl)amino]ethyl}pyrazolidin-3-ones 12a-c, three-step selective alkylation of the amidic N-2 to give 2-alkyl-5-{2-[(alkyl)(benzyloxycarbonyl) amino]ethyl}pyrazolidin-3-ones 16b-h, followed by hydrogenolytic Cbz-deprotection and subsequent cyclization of the intermediate 1,4-diamine with CDI to furnish the title compounds 3. Most of the synthetic steps were performed as a one-pot transformation. Georg Thieme Verlag Stuttgart New York.

Ultrasound-assisted aza-Michael reaction in water: A green procedure

The conjugate addition of amines to conjugated alkenes (commonly known as aza-Michael reaction) constitutes a key step for the synthesis of various complex natural products, antibiotics, α-amino alcohols and chiral auxiliaries. Ultrasound-induced addition of several amines to α, β-unsaturated ketones, esters and nitriles has been carried out very efficiently in water as well as under solvent-free conditions. No catalysts or solid supports have been used in this method. Remarkable enhancement of reaction rate has been observed in water under ultrasound-induced method. This environmentally benign procedure has provided clean formation of the products with better selectivity.

Synthesis and characterization of N-substitutional ethylenediamine derivatives

N-Substituted and N,N-disubstituted ethylenediamine derivatives were prepared rapidly in aqueous conditions from 30 to 76 % yields, respectively, on a multi-gram scale starting from inexpensive and commercially available starting materials. The steps involved Michael addition, hydrazinolysis and Curtius rearrangements. The highlight of this method lies on its convenience and economy in accessing these intermediates.

Sterically controlled stereoregulation in aldol reactions of 3-aryl-1-alkyl dihydrothiouracils

Aldol reactions of 3-aryl-1-alkyl dihydrothiouracils were investigated with respect to the orientation of the exocyclic group at N1, electronic effects of the aryl substituent at N3 and the steric demands of the electrophile. The reactions highlight the preference for formation of the anti aldol diastereomer with increasing steric constraints of the reactants. Georg Thieme Verlag Stuttgart · New York.

Microwave-induced aza-michael reaction in water: A remarkably simple procedure

Microwave-induced fast addition of several amines to conjugated carbonyl compounds has been carried out in water very efficiently in the absence of any catalyst. Copyright

Aza-michael addition of amines to α,β-unsaturated compounds using molecular iodine as catalyst

Aza-Michael adducts are obtained in very good yields by the conjugate addition of aliphatic amines to α,β-unsaturated compounds using molecular iodine as catalyst in dichloromethane at room temperature. Aromatic amines were found to be reactive under reflux in toluene.