700269-31-4

Usage

Compound type

2(1H)-Pyrazinone derivative

Substituents

Ethoxy group, methyl group, phenylethyl group

Stereochemistry

(3S)configuration

Potential applications

Pharmaceutical (anti-inflammatory and analgesic activities)

Importance of stereochemistry

Impacts biological activity and interactions with other molecules

Need for further research

To fully understand properties and potential uses

Upstream product

• 368-39-8 triethyloxonium fluoroborate 

Downstream Products

• 357666-55-8 (1S,4S)-1-ethoxy-4-methyl-2-phenethyl-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-dione 
• 357666-75-2 (-)-(4S)-4-methyl-2-phenethyl-2,4-dihydropyrazino[2,1-b]quinazoline-1,3,6-trione 

Relevant academic research and scientific papers

Microwave-assisted, solvent-free synthesis of several quinazoline alkaloid frameworks

Microwave irradiation leads to a considerable improvement of the cyclocondensation between anthranilic acid and lactim ethers derived from piperazine-2,5-diones in terms of reaction times, yields, and stereocenter integrity. This reaction has been used to

Intramolecular friedel-crafts-type reactions involving N-acyliminium ions derived from glycine templates

Enantiomerically pure 4-substituted 2-aralkyl-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-diones (1b-m) in which the alkyl chain is (CH2)n, n = 1-3, behave as glycine templates giving by treatment with [hydroxy(tosyloxy)iodo]benzene in ethyl acetate cis-1-tosyloxy derivatives. When these compounds contain electron-rich aryl substituents with n = 2, they spontaneously cyclize through intramolecular Friedel-Crafts-type diastereoselective reactions to give penta- or hexacyclic compounds. Otherwise, they give by solvolysis cis-1-alkoxy derivatives, which in a second step, may be cyclized in acid if n = 2, 3. All these reactions must occur through N-acyliminium species in SN1-like mechanisms. 1-Alkoxy-2-arylmethyl derivatives are reluctant to cyclize, giving trans-1-hydroxy compounds as the only isolated reaction products.