Recent synthetic scenario on imidazo[1,2-a]pyridines chemical intermediate

Abstract

Of the biologically important benzene fused heterocycles, the most important are those containing a ring-junction nitrogen. The majority of ring junction systems do not occur naturally, but they have been important from a theoretical viewpoint, for preparation of potentially active analogues. The imidazo[1,2-a] pyridines are an important class of nitrogen ring junction heterocyclic compounds. They have huge applications in medicinal chemistry and drug molecule production. Thus, the initial discussion focuses on synthetic strategies of imidazo[1,2-a] pyridines, and later we disclose the reactivity of the imidazo[1,2-a]pyridines. This review is intended to summarize and discuss the most recent developments of synthesis and reactivity of imidazo[1,2-a]pyridines, mainly the contributions after 2007.

Regioselective Base‐controlled Pd‐catalyzed Arylation of Imidazo[1,2‐a]pyridines: leading selectivity at C8 position by N‐chelation over O‐chelation

“…On the other hand, imidazo[1,2‐ a ]pyridine skeletons are widely present in many natural [9] and pharmaceutical products [10] . Imidazo[1,2‐ a ]pyridine derivatives have been reported for various biological activities including antibacterial, [11] antifungal, [12] antiviral, [13] anti‐inflammatory, [14] antipyretic, and analgesics [15] .…”

“…[7] Very recently Shi and Co-workers also established Pd(0) catalyzed methodology for the C4 arylation by using the removable directing group. [8] On the other hand, imidazo[1,2-a]pyridine skeletons are widely present in many natural [9] and pharmaceutical products. [10] Imidazo[1,2-a]pyridine derivatives have been reported for various biological activities including antibacterial, [11] antifungal, [12] antiviral, [13] anti-inflammatory, [14] antipyretic, and analgesics.…”

Recent Advances in Transition-Metal-Free Late-Stage C-H and N-H Arylation of Heteroarenes Using Diaryliodonium Salts

“…Eco-friendly late-stage C-H functionalization of these N -bearing polycyclic scaffolds has emerged as a powerful strategy for the synthesis of libraries of highly valuable compounds. Indeed, 3-substituted imidazo[1,2- a ]pyridines are attractive compounds in drug development exhibiting various pharmacological activities as well as in optoelectronic devices [ 65 , 66 , 67 ]. The direct C3-arylations were performed in the presence of t BuOK (2.0 equiv) as a base in acetonitrile at 60 °C for 24 h ( Scheme 7 ).…”

Synthesis, study of antileishmanial and antitrypanosomal activity of imidazo pyridine fused triazole analogues

“…[7][8][9] The imidazo-[1,2-a]-pyridine core is present in some established drugs (Fig. 1), such as alpidem (anxiolytic), 10 zolpidem (hypnotic), 11 saripidem (sedative and anxiolytic), 12 zolimidine (anti-ulcer), 13 olprinone (to treat acute heart failure), 14 minodronic acid (to treat anxiety, heart failure, osteoporosis), 15 and Soraprazan (anti-ulcer). 16 It is also present in some biologically active derivatives such as GSK812397 (CXCR4 antagonist), 17 PI3K-a inhibitors, 18 positive allosteric modulators of mGlu2 receptors, 19 TNF-a inhibitors (Fig.…”