76311-92-7

Upstream product

• 123-75-1 pyrrolidine 
• 37517-81-0 3-chloro-3-oxopropanoic acid methyl ester 
• 108-59-8 malonic acid dimethyl ester 
• 99054-21-4 7-Azido-3-oxo-heptanoic acid methyl ester 

Downstream Products

• 1193366-14-1 3-(pyrrolidin-1-yl)-3-oxopropanamide 
• 1173290-80-6 3-(6-bromo-2-methoxy-quinolin-3-yl)-3-phenyl-2-(pyrrolidine-1-carbonyl)-propionic acid methyl ester 

Relevant academic research and scientific papers

Tetrahydro-1,3-oxazepines via Intramolecular Amination of Cyclopropylmethyl Cation

An efficient synthesis of tetrahydro-1,3-oxazepines was developed involving the regioselective intramolecular amination of cyclopropylmethyl cation. The cation was generated by the abstraction of one imidate group in bis-imidate bearing a carbocation-stabilizing substituent. Using 1,1,2,3-tetrasubstituted cyclopropane substrates, highly diastereoselective intramolecular amination to trans-tetrahydro-1,3-oxazepines was achieved. The resulting tetrahydro-1,3-oxazepines were transformed to the homoallylamine derivatives in high yields.

Facile and versatile room-temperature synthesis of N,n-disubstituted cyanoacetamides from malonic ester chloride

A general method for the synthesis of various N,N-disubstituted cyanoacetamides from readily available methyl malonyl chloride and secondary amines, including sterically demanding aliphatic and aromatic amines, is described.

trans-directing ability of amide groups in cyclopropanation: Application to the asymmetric cyclopropanation of alkenes with diazo reagents bearing two carboxy groups

(Chemical Equation Presented) Highly stereoselective: A highly enantioselective (up to 97 % ee) and diastereoselective (>30:1 d.r.) Rh II-catalyzed cyclopropanation of alkenes using a diazo reagent bearing two carboxy groups is described. This new methodology exploits the powerful trans-directing ability of amides to improve enantiocontrol. Mono- and disubstituted olefins are cyclopropanated in good yields. nttl=N-1,8-naphthoyl- tert-leucine.

Synthesis of some 4-oxothiochromenes and related compounds

Thiosalicylic acids react with 2-substituted N,N-dialkyl acetamides to give 3-substituted-N,N-dialkyl-2-amino-4-oxothiochromenes 13. N-Alkyl 2-piperidone and analogous caprolactams give derivatives of 1,2,3,4-tetrahydrothiochromeno[2, 3-b]pyridin-5-one 16

Synthesis of amides from esters and amines under microwave irradiation

Formamide, primary and secondary amines react with esters in the presence of potassium tert-butoxide under microwave irradiation. Substituted amides are formed in yields (generally more than 70%) much higher than under conventional heating.

Intramolecular Schmidt reactions of alkyl azides with ketones: Scope and stereochemical studies

The intramolecular Schmidt reaction of alkyl azides and ketones has been demonstrated. The reaction is proposed to occur via initial attack of an azide on a ketone activated by a variety of protic or Lewis acids, including trifluoroacetic acid, titanium tetrachloride, and others. The resulting azidohydrin undergoes a direct rearrangement to afford the product amide and molecular nitrogen. When cyclic ketones are used, fused bicyclic lactams of types encountered in a wide variety of natural products are obtained. Although the distance allowed between the carbonyl group and the alkyl azide is quite restricted, the reaction is general with respect to the ketone component, including acyclic ketones and cyclic substrates ranging from standard to large ring sizes. The reaction also succeeds with aldehydes, although elimination or hydride migration products compete. In several cases examined the reaction was found to proceed with retention of configuration at the migrating carbon. Competing reactions with β-diketones and α,β-unsaturated ketones were found to predominate over ring expansion.

THE SYNTHESIS OFβ-LACTONES AND β-LACTAMS FROM MALONATES AND MALONAMIDES

The rhodium diacetate induced insertion reactions of some simple esters and amides of diazomalonic acid result in the formation of β-lactones and β-lactams.