Acetyl cyanide as a cyanide source in a tandem catalyst-free modified Groebke–Blackburn–Bienaymé [4+1]-cycloaddition-Strecker cascade

The Groebke‐Blackburn‐Bienaymé Reaction

“…1:1:1 CHCl 3 /TMOF/MeOH [40] 1 TFE [32,180] Solvents such as DMSO, DMF and PEG-400 are in general not the solvents of choice because of their high boiling points and difficulties to remove during workup ( Table 5). They prove, however, to be quite useful when solubility issues with highly polar starting materials are present such as the aforementioned amidine containing nucleobases.…”

Aminoazole-Based Diversity-Oriented Synthesis of Heterocycles

“…There are a lot of examples of using aminoazoles as an amine component in GBB-3CR resulting in the formation of heterocycles like 181 . The most studied ones are the processes involving 3-amino-1,2,4-triazoles (Bienaymé and Bouzid, 1998 ; Tyagi et al, 2012 ; Urich et al, 2013 ; Aouali et al, 2015 ), 2-amino(benzo)thiazoles (Bienaymé and Bouzid, 1998 ; Guchhait and Madaan, 2009 , 2010 ; Guchhait et al, 2009 ; Al-Tel et al, 2010 ; Akritopoulou-Zanze et al, 2011 ; Baviskar et al, 2011 ; Burchak et al, 2011 ; Hieke et al, 2012 ; Tyagi et al, 2012 ; Vidyacharan et al, 2014 ; Martinez-Ariza et al, 2015 ; Ansari et al, 2016 ; Shaabani and Hooshmand, 2016 ; Shao et al, 2017 ), 2-amino-1,3,4-thiadiazoles (Krasavin et al, 2008 ; Guchhait and Madaan, 2009 ; Guchhait et al, 2009 ; Wadhwa et al, 2015 ), 2-amino(benz)imidazoles (Lee et al, 2013 ; Pereshivko et al, 2013 ). GBB-3CR involving 2-aminooxazoles (Bienaymé and Bouzid, 1998 ) led to the formation of imidazoazoles while involving 1,2,5-oxadiazole-3,4-diamine (Kysil et al, 2010 ) gave oxadiazolopyrazines.…”

Synthesis of imidazo[1, 2‐a]pyridines via the silver acetate‐catalyzed Groebke‐Blackburn‐Bienayme reaction with ethylene glycol as a biodegradable and sustainable solvent

“…[4][5][6][7] This reaction has been widely used for the synthesis of bioactive compounds with a broad spectrum of pharmacological and biological applications, such as antiviral, antibacterial, fungicidal, and antiinflammatory properties. [8][9][10][11][12] Because of these properties, the imidazo[1,2-a]pyridine (IPY) scaffold was used as an important moiety in many commercially available drugs, such as zolpidem (insomnia treatment drug), alpidem (anxiolytic drug), olprinone (acute heart failure treatment), zolimidine (an anti-peptic ulcer drug), and the optically active drug GSK812397 (anti-HIV infection) [13][14][15][16][17] (Figure 1). In addition, some of the imidazo [1, 2-a] pyridines show fluorescence under the ultraviolet light, which interfered with the enzymatic assay; therefore, this moiety could also be used in fluorescent dyes.…”