‘Click Synthesis’ of Some Novel O‐Substituted Oximes Containing 1,2,3‐Triazole‐1,4‐diyl Residues as New Analogs of β‐Adrenoceptor Antagonists

Abstract

The ‘click synthesis’ of some novel O‐substituted oximes, 7a–7t, which contain 1,2,3‐triazolediyl residues, as new analogs of β‐adrenoceptor antagonists is described (Schemes 1–4). The synthesis of these compounds was achieved in four to five steps. The formation of oximes of 9H‐fluoren‐9‐one and benzophenone, i.e., 9a and 9b, respectively, followed by their reaction with propargyl bromide, afforded O‐propargyl oximes 10a and 10b, respectively, which by a subsequent CuI‐catalyzed Huisgen cycloaddition with prepared β‐azido alcohols 11a–11j (Schemes 2 and 3), led to the target compounds 7a–7t in good yields.

Design, synthesis and biological evaluation of novel 1,2,3-triazolyl $$\upbeta $$ β -hydroxy alkyl/carbazole hybrid molecules

“…The β-azido Alcohols 13a-13n were prepared by our previously described method in the literature [37,38].…”

“…3) [25,26,31,32]. Therefore, with inspiration from the remarkable biological activities of 1,2,3-triazole and carbazole and also in continuation of our interest in discovering the new azole bioactive compounds [33][34][35][36][37][38][39][40], herein we would like to report the design and synthesis of some 1,2,3-triazolyl β-hydroxy alkyl/carbazole hybrids as a new type of antifungal agent (Fig. 3).…”

Review of the synthesis of acyclic and cyclic oxime ethers

“…The attempts to synthesis of O-propargylated oximes 16a,b with treatment of oximes 14 with propargyl bromide 15 in the presence of KOH in DMSO/H 2 O 9 : 1 resulted in products with higher than 86% yield (Scheme 4). 106…”

Fluoren-9-one oxime

“…(2014). E70, o265 The title compound, which was prepared according to a known procedure (Moore & Huntress, 1927) has found extensive use as a starting material for preparation of medicinal active compounds such as novel cyclophilin A inhibitors (Ni et al, 2009), novel analogs of beta-adrenoceptor antagonists (Rad et al, 2012) and beta-blocker (Amlaiky et al, 1983).…”