Topic
Bicyclic molecule
About: Bicyclic molecule is a research topic. Over the lifetime, 29587 publications have been published within this topic receiving 451252 citations. The topic is also known as: bicyclic molecule.
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93 citations
TL;DR: Replacement of the enamine functionality of the hit series with either an imidazole or a pyrazole ring led to compounds that inhibited both capsid assembly and reverse transcriptase, leading to lead compound 48, a pure capsidAssembly inhibitor with improved antiviral activity.
93 citations
TL;DR: In this paper, a radical mechanism was used to obtain a (tetrahydrofuranylmethyl)zinc halide of type 1, which can be reacted with various electrophiles after a transmetalation with CuCN·2LiCl.
Abstract: Unsaturated iodo or bromo acetals of type 2 undergo a smooth cyclization mediated by diethylzinc (2 equiv) and Ni(acac)2 as catalyst (2−5 mol %). These cyclizations proceed via a radical mechanism affording a (tetrahydrofuranylmethyl)zinc halide of type 1, which can be reacted with various electrophiles after a transmetalation with CuCN·2LiCl. High stereoselectivities are usually observed in the ring closures, especially if monocyclic cyclization precursors are used. In these cases, bicyclic products of the endo-configuration are obtained with over 94% diastereoselectivity. The synthetic method has been extended to the preparation of a nitrogen heterocycle and over 98% pure trans-4,5-disubstituted γ-butyrolactones. A short enantioselective synthesis of (−)-methylenolactocine (3) using the radical cyclization and a novel oxidation of α-silyl zinc peroxide as a key step is also described.
93 citations
93 citations
TL;DR: In this article, a method of synthesizing fused ring pyridines (annulated) by co-oligomerization of α,ω-diynes with about molar equivalents of nitriles using a Co+1 catalyst preferably cyclopentadienyl cobalt dicarbonyl was presented.
Abstract: A method of synthesizing fused ring pyridines (annulated) by co-oligomerization of α,ω-diynes with about molar equivalents of nitriles using a Co+1 catalyst preferably cyclopentadienyl cobalt dicarbonyl. Additionally, new compounds of tricyclic quinolizine-4-ones were produced where excess cyanoacetic ester starting materials were utilized (about 2:1 equivalent nitriles:diyne). The results with the catalyst employed indicated a stepwise mechanism in which cobalt(I) catalyst first forms a metallocycle intermediate derived from the bisacetylene. This cobalt(III) intermediate reacts preferentially with nitriles to give the product annulated pyridines in good yield. Generally, preferred conditions indicated roughly molar equivalents of reactants with no substantial excess of either reactant for the bicyclic compounds. Preferred conditions include a moderate temperature (solvent reflux temperature) and a preferred solvent such as BTX-type solvent (xylene) or an alkane (N-octane) under an inert blanket (nitrogen) for a multi-day period.
92 citations