Unknown

Dataset Information

0

Unnatural ?-amino ethyl esters from diethyl malonate or ethyl ?-bromo-?-hydroxyiminocarboxylate.

ABSTRACT: We have explored here the scope of the age-old diethyl malonate-based accesses to ?-amino esters involving Knoevenagel condensations of diethyl malonate on aldehydes, reductions of the resulting alkylidenemalonates, the preparation of the corresponding ?-hydroxyimino esters and their final reduction. This synthetic pathway turned out to be general although some unexpected limitations were encountered. The synthetic modifications of some of the intermediates - using Suzuki-Miyaura coupling or cycloadditions - before undertaking the oximation step - provided accesses to further ?-amino esters. Moreover, other pathways to ?-hydroxyimino esters were explored including an attempt to improve the cycloadditions between ethyl ?-bromo-?-hydroxyiminocarboxylate and various alkylfuranes.

SUBMITTER: Coutant EP 

PROVIDER: S-EPMC6244313 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

Unnatural α-amino ethyl esters from diethyl malonate or ethyl β-bromo-α-hydroxyiminocarboxylate.

Coutant Eloi P EP   Hervin Vincent V   Gagnot Glwadys G   Ford Candice C   Baatallah Racha R   Janin Yves L YL  

Beilstein journal of organic chemistry 20181116

We have explored here the scope of the age-old diethyl malonate-based accesses to α-amino esters involving Knoevenagel condensations of diethyl malonate on aldehydes, reductions of the resulting alkylidenemalonates, the preparation of the corresponding α-hydroxyimino esters and their final reduction. This synthetic pathway turned out to be general although some unexpected limitations were encountered. The synthetic modifications of some of the intermediates - using Suzuki-Miyaura coupling or cyc  ...[more]

Similar Datasets

Unknown Diethyl 2-[(4-bromo-anilino)methyl-idene]malonate.
| S-EPMC3011394 | biostudies-literature
Unknown Synthesis of unnatural ?-amino esters using ethyl nitroacetate and condensation or cycloaddition reactions.
| S-EPMC6244114 | biostudies-other
Unknown Diethyl 2-{[(4-meth-oxy-3-pyrid-yl)amino]-methyl-idene}malonate.
| S-EPMC3212332 | biostudies-literature
Unknown Diethyl 2-{4-diethyl-amino-2-[(dimethyl-carbamothio-yl)-oxy]benzyl-idene}malonate.
| S-EPMC3151902 | biostudies-other
Unknown Diethyl 2-(triphenyl-meth-yl)malonate.
| S-EPMC3257068 | biostudies-literature
Unknown (E)-Ethyl 4-[4-(diethyl-amino)styr-yl]benzoate.
| S-EPMC2915316 | biostudies-literature
Unknown {2-Bromo-4-chloro-6-[2-(diethyl-amino)ethyl-imino-meth-yl]phenolato-?N,N',O}(thio-cyanato-?N)copper(II).
| S-EPMC2915066 | biostudies-literature
Unknown Diethyl 2-(2-nitro-benzyl-idene)malonate.
| S-EPMC2969968 | biostudies-literature
Unknown 2-{[2,2-Bis(diethyl-amino)-ethan-2-ylium-thio-yl]sulfan-yl}-1,1-bis-(diethyl-amino)-ethyl-ium bis-(perchlorate).
| S-EPMC3435765 | biostudies-literature
Unknown On the hydrolysis of diethyl 2-(perfluorophenyl)malonate.
| S-EPMC7404147 | biostudies-literature