112753-91-0

Upstream product

• 112753-90-9 N-cinnamoyl-2,2-dimethylaziridine 
• 126437-19-2 1-cinnamoyl-2,2-dimethylaziridine 
• 23522-65-8 2,2,2-trichloroethyl 3-phenylpropionate 
• 78-81-9 isobutylamine 
• 1873-29-6 isobutyl isocyanate 
• 365441-87-8 3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-methylpropanoic acid 
• 501-52-0 3-Phenylpropionic acid 

Relevant academic research and scientific papers

Practical one-pot amidation of N -Alloc-, N -Boc-, and N -Cbz protected amines under mild conditions

A facile one-pot synthesis of amides from N-Alloc-, N-Boc-, and N-Cbz-protected amines has been described. The reactions involve the use of isocyanate intermediates, which are generated in situ in the presence of 2-chloropyridine and trifluoromethanesulfonyl anhydride, to react with Grignard reagents to produce the corresponding amides. Using this reaction protocol, a variety of N-Alloc-, N-Boc-, and N-Cbz-protected aliphatic amines and aryl amines were efficiently converted to amides with high yields. This method is highly effective for the synthesis of amides and offers a promising approach for facile amidation.

Facile direct synthesis of amides from trichloroethyl esters using catalytic DBU

A practical method for the direct synthesis of amide compounds is described. Using small quantities of DBU as a catalyst, the direct conversion of 2,2,2-trichloroethyl esters to their corresponding amides was readily achieved. Based on this protocol, various amide compounds were successfully synthesized in high yield, suggesting a promising approach for the practical one-pot aminolysis from 2,2,2-trichloroethyl protected esters.

Amides in one pot from Carboxylic Acids and Amines via Sulfinylamides

An efficient method has been developed for the direct amidification of carboxylic acids via sulfinylamides preformed in situ by the reaction of pure amines with prop-2- ene-1-sulfinyl chloride. The method can be applied to aliphatic acids, including pivalic acid, aromatic acids, and primary and secondary amines. It is compatible with acids bearing unprotected alcohol, phenol, and ketone moieties and applicable to the synthesis of peptides. It does not induce their a-epimerization.

Evolutions differentes de radicaux anions formes par voie chimique ou electrochimique

Chemical and electrochemical reductions of N-aroylaziridines 1 are described and compared.The first step is a single electron transfer (1 +e -> 1-. -> 1'-.).But compounds obtained from 1'-. are depending on the method used way followed: chemical reduction of N-cinnamoylaziridine 1e provides pyrrolidone 10e; but oxazoline 11e is available by electrochemical reduction of the same starting material 1e.Counter ion seems responsible of these different results.In agreement with this hypothesis, it is shown that pyrrolidone 10e is obtained from 1j only in presence of a counter ion.

HOMOLYTIC AZIRIDINE OPENING (AZA VARIANT OF CYCLOPROPYLCARBINYL-HOMOALLYL REARRANGEMENT) BY ADDITION OF TRIBUTYLTIN RADICAL TO N-ACYLAZIRIDINES. FACTORS CONTRIBUTING TO THE REGIOSELECTIVITY

AIBN initiated reaction of N-acylaziridines 1 with Bu3SnH in refluxing benzene provided products 5 and 8 of reductive ring opening.Yields (practically quantitative in most cases) fell drastically with steric hindrance of the addition of Bu3Sn to the acyl oxygen of 1.They depended to some extent on the experimental conditions for hydrogen capturing when aziridine homolysis provided a primary radical 3 or 6.The regioselectivity of (probably reversible) ring homolysis can be understood in terms of the stability of the arising radical (3, 6), of stereoelectronic control (e.g. 1i as compared to 1h) and of frontier orbital interactions (1j).A possible difference in bond lengths as explanation for the formation of the primary radical from 1j did not find support from an X-ray structure analysis of N-tosyl-2-methyl-aziridine 11.Isomeric products were obtained only twice (1i, 1j) with a dependence of the ratio 5j:8j on concentration and hydrogen isotope of Bu3SnH.No such dependence was found for the ratio 5:14 (reduction without and with an intervening cyclization of 3 leading to a pyrrolidone) obtained from the N-cinnamoylaziridine 1l.This ratio (1:9 for 1l and 1:3 for 1n) must reflect the E-Z isomers in 3.The observed preference for the formation of E-3 from 2 can be explained by stereoelectronic and steric effects.A cinnamoyl double bond in 5 was saturated depending on experimental conditions.

INTRAMOLECULAR RADICAL TRAPPING IN "SET" RING OPENING OF N-ENOYL AZIRIDINES. A NEW MECHANISTIC PROBE AND A NEW SYNTESIS OF PYRROLIDONES.

N-Acryloyl aziridines 1a-c form pyrrolidones 4a-c via electron attachment, homolytic ring cleavage of the intermediate ketyl, and intramolecular trapping of the radical by the C=C bond of the acryloyl moiety of 1a-c.