ChemInform Abstract: PURINES, PYRIMIDINES, AND IMIDAZOLES. PART 61. REACTION OF 6-ALKYLAMINO-4-CHLORO-5-NITROPYRIMIDINES WITH DIETHYL MALONATE, ETHYL CYANOACETATE, AND ETHYL ACETOACETATE AND SOME DERIVED PYRROLO(3,2-D)PYRIMIDINES RELATED TO THE CYTOKININS

1985 ◽  
Vol 16 (17) ◽  
Author(s):  
S. GREGSON ◽  
G. SHAW
1987 ◽  
Vol 65 (12) ◽  
pp. 2717-2721 ◽  
Author(s):  
Sham S. Gandhi ◽  
Martin S. Gibson

1,1-Dimorpholinoethene and 1,1-dipiperidinoethene condense with such compounds as malononitrile, ethyl cyanoacetate, cyanoacetamide, and diethyl malonate to give the corresponding β,β-disubstituted enamine, a molecule of morpholine or piperidine being eliminated in the process. Similar reactions with acetylacetone and ethyl acetoacetate proceed with loss of the acetyl group to give the β-substituted enamine. 1,1-Dipiperidinoethene and nitromethane give the β-nitroenamine. Secondary processes of either hydrolysis or further Michael addition and elimination are noted in condensations of 1,1-dimorpholinoethene or 1,1-dipiperidinoethene with cyanoacetamide under more basic conditions.1,1-Dipiperidinoethene is arylated at the 2-position by 2,4-dinitrochlorobenzene.


2019 ◽  
Vol 2019 ◽  
pp. 1-10 ◽  
Author(s):  
Nagy M. Khalifa ◽  
Mohamed A. Al-Omar ◽  
Hamad M. Alkahtani ◽  
Ahmed H. Bakheit

A new class of pyridopyrimidinone compounds containing different nitrogenous heterocycles were synthesized starting from the key precursor 2-hydrazinyl-5-phenyl-7-(pyridin-3-yl)pyrido[2,3-d]pyrimidin-4(3H)-one via condensation with series of aromatic aldehydes and cyclization using different reagents as ethyl acetoacetate, ethyl cyanoacetate, diethyl malonate, and ammonium isothiocyanate. The bioassay results showed compound 6 to be highly effective towards three human cancer cell lines (HepG2, PC-3, and HCT-116) in vitro with promising activity values (IC50: 0.5 μM) relative to the standard doxorubicin (IC50: 0.6 μM). Kinase inhibitory evaluation of compound 6 displays hopeful inhibitory action against BRAF V600E, EGFR, and PDGFRβ at100 μM. The molecular docking studies supported the initial kinase assay.


1993 ◽  
Vol 58 (9) ◽  
pp. 2215-2221 ◽  
Author(s):  
Abd El-Hamid N. Ahmed

2-Methyl[3,1]benzoxazin-4-one (I) is easily accessible , but its chemistry has not been investigated enough. Structure similarity between I and phthalic anhydride encouraged us to investigate the reaction of I with compounds bearing active methylenes namely diethyl malonate, ethyl acetoacetate and acetylacetone in presence of zinc chloride, Thus new compounds II, III and IV were synthesized. Those compounds were used as precursors for the synthesis of various spiroheterocycles.


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