Fluorescent annulated imidazo[4,5-c]isoquinolinesviaa GBB-3CR/imidoylation sequence – DNA-interactions in pUC-19 gel electrophoresis mobility shift assay

Abstract

Herein we report the development of a sequential synthesis route towards annulated imidazo[4,5 c]isoquinolines comprising a GBB 3CR, followed by an intramolecular imidoylative cyclisation X-Ray crystallography revealed a flat 3D...

Synthesis of Fused Imidazoles and Pyrimidinones from 2‐Aminoazines

“…In the syntheses of compounds 11 – 12 and compounds 15 – 21 , 2‐aminoazines such as pyridine‐2‐amine ( 1 a ), pyrimidin‐2‐amine ( 1 b ), pyrimidin‐4‐amine ( 1 c ) and pyrazin‐2‐amine ( 1 d ) were used. Several catalysts, including lanthanum triflate (La(OTf) 3 ) (compound 12 ), [17] scandium tris(trifluoromethanesulfonate) (Sc(OTf) 3 ) (compounds 16 and 19 ), [18] ytterbium triflate (Yb(OTf) 3 ), [19] calcium triflate (Ca(OTf) 2 ) (compound 14 ), [20] perchloric acid (HClO 4 ) (compound 20 ), [21] acetic acid (compounds 11 , 13 and 21 ), [22] hydrogen chloride (compounds 17 and 22 ), [23,24] trifluoracetic acid (TFA), (Compound 18 ), [25] and sodium dodecyl sulphate (SDS) [26] have been used to promote the GBB reaction with high product yield. Biocatalysts, such as lipase enzymes, have also been used in the GBB reaction [27] .…”

“…The reaction is compatible with a wide range of 2-aminoazines, aldehydes, and isonitriles. Numerous reaction conditions have been investigated, including a diversity of catalysts, solvent or solvent-free conditions, microwave irradiation, and conven- (compound 12), [17] scandium tris(trifluoromethanesulfonate) (Sc(OTf) 3 ) (compounds 16 and 19), [18] ytterbium triflate (Yb(OTf) 3 ), [19] calcium triflate (Ca(OTf) 2 ) (compound 14), [20] perchloric acid (HClO 4 ) (compound 20), [21] acetic acid (compounds 11, 13 and 21), [22] hydrogen chloride (compounds 17 and 22), [23,24] trifluoracetic acid (TFA), (Compound 18), [25] and sodium dodecyl sulphate (SDS) [26] have been used to promote the GBB reaction with high product yield. Biocatalysts, such as lipase enzymes, have also been used in the GBB reaction.…”

Synthesis of Imidazo[1,2-a]pyridine-Fused 1,3-Benzodiazepine Derivatives with Anticancer Activity via a One-Pot Cascade GBB-3CR/Pd(II)-Catalyzed Azide-Isocyanide Coupling/Cyclization Process

“…For example, a transition-metal-free synthesis of spiro­[chromene-imidazo­[1,2- a ]­pyridin]-3′-imines was discovered by a post-GBB/6- exo -dig cyclization reaction under mild conditions . Subsequently, Stahlberger and co-workers have developed a sequential synthesis route toward annulated imidazo­[4,5- c ]­isoquinolines via a novel GBB-3CR/imidoylative Hartwig–Buchwald amination sequence . In the past decades, isocyanides and azides have been known as versatile synthetic intermediates in organic synthesis .…”

“…15 Subsequently, Stahlberger and co-workers have developed a sequential synthesis route toward annulated imidazo [4,5-c]isoquinolines via a novel GBB-3CR/ imidoylative Hartwig−Buchwald amination sequence. 16 In the past decades, isocyanides and azides have been known as versatile synthetic intermediates in organic synthesis. 17 In this field, the azide-isocyanide cross-coupling reaction has emerged as an efficient and highly atom-economical method for the construction of functionalized carbodiimides which afford diverse N-containing heterocycles.…”

Synthesis of pyrazolo[5′,1′:2,3]imidazo[1,5-c]quinazolin-6(5H)-ones and molecular docking study of their affinity against the COVID-19 main protease

“…14,15 One of the important classes of MCRs used for the one-pot synthesis of the fused imidazoles is Groebke-Blackburn-Bienaymé reaction (GBBR). 16,17 In this reaction, imidazopyridines are synthesized using raw materials including an aldehyde, an isocyanide, and a heterocyclic compound containing an amidine fragment in the presence of various catalysts. 18 Recently, several groups have improved this reaction and obtained various types of N-fused heterocyclic compounds by changing starting materials using different catalysts.…”