95838-55-4

Upstream product

• 34840-23-8 1,3-Dicarbomethoxy-S-methylisothiourea 
• 117358-89-1 3-Carbomethoxy-5-nitro-2-oximino-4-phenylpentane 
• 91473-85-7 5-[1-Methoxycarbonyl-2-oxo-prop-(Z)-ylideneamino]-2,5-dimethyl-4-phenyl-4,5-dihydro-furan-3-carboxylic acid methyl ester 
• 102-96-5 (2-nitroethenyl)benzene 
• 14205-39-1 methyl 3-aminocrotonate 
• 105-45-3 acetoacetic acid methyl ester 
• 579-07-7 1-Phenylpropane-1,2-dione 
• 6078-06-4 (R)-methyl 3-aminobutanoate hydrochloride 
• 5303-65-1 3-aminobutanoic acid ethyl ester 
• 705-60-2 (2-nitroprop-1-enyl)benzene 
• 21731-17-9 methyl 3-aminocrotonate 
• 4187-87-5 1-Phenyl-2-propyn-1-ol 
• 117358-87-9 Methyl 3-amino-2-<2-nitro-1-phenylethyl>crotonate 
• 81675-18-5 methyl 2-acetyl-4-nitro-3-phenylbutyrate 

Relevant academic research and scientific papers

Transaminase-Mediated Amine Borrowing via Shuttle Biocatalysis

Shuttle catalysis has emerged as a useful methodology for the reversible transfer of small functional groups, such as CO and HCN, and goes far beyond transfer hydrogenation chemistry. While a biocatalytic hydrogen-borrowing methodology is well established, the biocatalytic borrowing of alternative functional groups has not yet been realized. Herein, we present a new concept of amine borrowing via biocatalytic shuttle catalysis, which has no counterpart in chemo-shuttle catalysis and allows efficient intermolecular amine shuttling to generate reactive intermediates in situ. By coupling this dynamic exchange with an irreversible downstream step to displace the reaction equilibrium in the forward direction, high conversion to target products can be achieved. We showcase the potential of this amine-borrowing methodology using a biocatalytic equivalent of both the Knorr-pyrrole synthesis and Pictet-Spengler reaction.

Chemo-Enzymatic Synthesis of Pyrazines and Pyrroles

Herein we report the biocatalytic synthesis of substituted pyrazines and pyrroles using a transaminase (ATA) to mediate the key amination step of the ketone precursors. Treatment of α-diketones with ATA-113 in the presence of a suitable amine donor yielded the corresponding α-amino ketones which underwent oxidative dimerization to the pyrazines. Selective amination of α-diketones in the presence of β-keto esters afforded substituted pyrroles in a biocatalytic equivalent of the classical Knorr pyrrole synthesis. Finally we have shown that pyrroles can be prepared by internal amine transfer catalyzed by a transaminase in which no external amine donor is required.

Synthesis of tetrasubstituted NH pyrroles and polysubstituted furans via an addition and cyclization strategy

The FeCl3-catalyzed addition and cyclization of enamino esters with nitroolefins provides a straightforward and general method for the synthesis of tetrasubstituted NH pyrroles. This novel method tolerates a wide range of functionality, and allows for rapid elaboration of the nitroolefins into a variety of substituted pyrroles in good yields. Further, an efficient KOAc-promoted addition and cyclization protocol toward substituted furans has been described as well. Georg Thieme Verlag Stuttgart · New York.

One-pot three-component synthesis of tetrasubstituted N - H pyrroles from secondary propargylic alcohols, 1,3-dicarbonyl compounds and tert-butyl carbamate

(Chemical Equation Presented) Several tetrasubstituted N - H pyrroles, functionalized with ester or ketone groups at C-3 position, were prepared by one-pot coupling of secondary propargylic alcohols with 1,3-dicarbonyl compounds and tert-butyl carbamate,

Reaction of N,N'-Dimethoxycarbonyl-S-methylisothiourea with Substituted Ethylenediamine and 1,4-Diaminobutane Derivatives

A stereoselective synthesis of methyl 4(5)-methyl-5(4)--4,5-dihydroimidazole-2-carbamate (4) and the unusual formation of 2,5-dimethyl-3-methoxycarbonyl-4-phenylpyrrole (14) in the reaction of N,N'-dimethoxycarbonyl-S-methylisoth

Heterocycles from α-Nitroolefins, VIII. - 2-Methyl-3-pyrrolecarboxylates from α-Nitroolefins and Acetoacetates

3-Pyrrolecarboxylates 4 can be prepared from α-nitroolefins 1 and acetoacetates 2 by two methods: (a) 1 and 2 react to give 4,5-dihydro-5-methyleneamino-3-furancarboxylates 3 which are hydrolyzed, (b) the nitronic acids 8, adducts of 1 and 2, yield with different reduction agents the heterocycles 4.