499766-65-3Relevant academic research and scientific papers
Experimental and theoretical FMO interaction studies of the Diels-Alder reaction of 5-acetyl-3-methythio-1,2,4-triazine with cyclic enamines
Lipińska, Teodozja
, p. 8148 - 8158 (2005)
Diels-Alder reaction of 5-acetyl-3-methylthio-1,2,4-triazine with five cyclic enamines has been reinvestigated in its preparative and theoretical aspects. Its regioselectivity has been developed practically, which is in agreement with theoretical consideration of the FMO interactions, including secondary orbital interactions in the transition state. Since the energetic demands are similar for all five pairs, it has been indicated that their reactivity differences can be explained by an influence of steric hindrance in the considered transition state. In result, the synthesis of the 3-acetyl-1-methylthiocycloalka[c]pyridines, as synthons for preparation of sempervirine and its analogues has been optimized. The subsequent side reaction has been detected as a serious problem, especially in the case of the six-membered enamine, which reacts with the acetyl group of the final product formed in the reaction mixture.
General route to the total synthesis of sempervirine analogues containing modified E rings, potential cytostatics
Lipińska, Teodozja
, p. 9565 - 9567 (2002)
Sempervirine analogues 13a-c with different E rings have been obtained via inverse electron demand Diels-Alder reactions of 5-acetyl-3-(methylsulfanyl)-1,2,4-triazine with cyclic enamines (formation of D and E rings) followed by Fischer indole synthesis u
One-Step Synthesis and Regioselective Alkylation of Substituted 1H-Pyrazolo[4,3-e] [1,2,4]triazine
Mojzych,Rykowski
, p. 1797 - 1803 (2007/10/03)
One-pot reaction between 5-acyl-3-(methylsulfanyl)-1,2,4-triazine (1) or its oxime (8) with hydrazine hydrochloride afforded 3-methyl-5-(methylsulfanyl)- 1H-pyrazolo[4,3-e][1,2,4]triazine (4) in good yield. Treatment of the latter with alkyl halides in th
