615581-28-7Relevant academic research and scientific papers
Synthesis of 3-(carboxyarylalkyl)imidazo[2,1-f][1,2,4]triazines as potential inhibitors of AMP deaminase
Kirkman, Joseph K.,Lindell, Stephen D.,Maechling, Simon,Slawin, Alexandra M. Z.,Moody, Christopher J.
supporting information; experimental part, p. 4452 - 4459 (2009/02/07)
C-Ribosyl 1,2,4-triazolo[1,2,4]triazines which are able to undergo covalent hydration are of interest as potential inhibitors of AMP deaminase. In a search for compounds with improved bioavailability we have synthesized compounds in which the sugar has been replaced by carboxyarylalkyl based ribose phosphate mimics. The target carboxyarylalkyl imidazotriazines 11 and 12 were synthesized using a linear seven step sequence starting from simple benzoate derivatives. Alternatively, the hydroxyethyl imidazotriazine 39 is available in five steps and this synthon was used to prepare the imidazotriazines 34 and 48 in a short convergent manner.
Samarium(II)-promoted radical spirocyclization onto an aromatic ring
Ohno, Hiroaki,Okumura, Mitsuaki,Maeda, Shin-Ichiro,Iwasaki, Hiroki,Wakayama, Ryutaro,Tanaka, Tetsuaki
, p. 7722 - 7732 (2007/10/03)
Samarium(II)-mediated spirocyclization onto an aromatic ring was achieved by the reaction of methyl 4-(4-oxoalkyl)benzoates with SmI2 in the presence of i-PrOH and HMPA, yielding methyl 1-alkyl-1-hydroxyspiro[4.5]dec-6-ene-8-carboxylates in moderate to high yields. Utilizing this chemistry, spiro[3.5] and -[5.5] systems, and sterically congested spiro[4.5] systems, were easily synthesized. For the successful conversion, appropriate activation of the aromatic ring has proven to be extremely important: while an ester or amide functionality on the aromatic ring can promote the spirocyclization, a sulfonamide substituent causes ortho cyclization.
