Synthesis of pyrrolidine-substituted benzamides via iodocyclization of β-enaminoesters

Novel 2-, and N-substituted 5-methylene-pyrrolidine benzamides and 2-, 3-, and N-substituted 5-methylene-2-pyrroline benzamides were synthesized for the first time in a straightforward manner and in good yields via iodocyclization of γ- and α-alkenyl-β-enaminoesters, respectively. The key step in the process is the synthesis of the methylene-pyrrolidine iodide and methylene-2-pyrroline iodide intermediates. Functional group inter-conversion of these iodides to their amino analogs, and their subsequent coupling to benzoic acids via EDC, afforded the above pyrrolidine/2-pyrroline-substituted benzamides in yields of around 75%.     

Synthesis and Single Crystal Structures of N-Substituted Benzamides and Their Chemoselective Selenation/Reduction Derivatives

A series of N-aryl-N-(2-oxo-2-arylethyl) benzamides and cinnamides has been prepared. The reaction of the benzamides with Woollins’ reagent, a highly efficient chemoselective selenation/reduction reagent, gave the corresponding N-aryl-N-(arylenethyl) benzoselenoamides in good yields. Five representative single crystal X-ray structures are discussed.     

Novel 1,2,3,4‐Tetrahydroquinazolinones via Reaction of 2‐Amino‐N‐substituted Benzamides and Dimethyl Acetylenedicarboxylate

Reaction of 2‐amino‐N‐substituted benzamides and dimethyl acetylenedicarboxylate (DMAD) in the presence of 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU) in H₂O at room temperature led to the formation of novel 1,2,3,4‐tetrahydroquinazolinones.     

High Pefpormance Liquid Chromatographic Determination of Some Substituted Benzamides in Serum After Ion-Pairing Extraction

Abstract

An assay was developed to identify and to quantify substituted benzamides in biological samples. After an organic extraction at acid pH in the presence of n-octyl sodium sulfate as counter-ion, high performance liquid chromatography was used to quantify these compounds. The molecules were detected by ultraviolet spectrophotometry (215 nm) and benzamides were also identified by tracing a complete U.V. spectrum directly on the eluted compound.

This method was successfully applies to specimens obtained from a child who ingested a large amount of metoclopramide.     

苯酰胺类D2受体显像剂的共平面效应

苯酰胺类化合物是多巴胺Ｄ2受体的拮抗剂,它不仅与Ｄ2受体的亲和力高,而且产生的锥体外副反应极轻,是一类很有应用潜力的抗精神病药物.放射性同位素(123Ｉ等)标记的苯酰胺类化合物可作为多巴胺Ｄ2受体显像剂用于临床诊断疾病.近年来,相继报导了一系列高亲和力的该类化合物,其中,123ＩＩＢＺＭ等已用于临床诊断疾病[1].本文在前文[2]苯酰胺类Ｄ2受体显像剂结构效应的研究基础上,利用ＳＹＢＹＬ6.4软件,研究了该类化合物分子的不同构象以及空间结构与结合活性之间的关系,证实了前文提出的由于分子内氢键形成六元共平面假想Ａ环、Ｂ环等是影响…     

Synthesis of Isoindolo[2,1‐a]quinazoline‐5,11‐dione Derivatives via the Reductive One‐Pot Reaction of N‐Substituted 2‐Nitrobenzamides and 2‐Formylbenzoic Acids

Various isoindolo[2,1‐a]quinazoline‐5,11‐dione derivatives 3 were synthesized in good yields by means of the reductive reaction of N‐substituted 2‐nitrobenzamides 1 and 2‐formylbenzoic acids 2 in the presence of SnCl₂?2 H₂O under reflux in EtOH (Scheme, Table). The procedure needed two steps, the reduction of the nitro group of the 2‐nitrobenzamide and ring closure by nucleophilic addition of the NH₂ group to both the formyl and carboxylic acid C?O groups.     

三价铑催化苯甲酰胺与醌的C–H活化偶联(英文)

三价铑在氧化条件下催化N-烷基苯甲酰胺与醌反应生成芳基醌.在氧化还原中性条件下,经过偶联和内酯化反应可以得到2-羟基-6H-苯并[c]吡喃-6-酮.     

Hydriodic Acid‐Mediated Cyclization of α‐Substituted Secondary 2‐Ethenylbenzamides: Synthesis of 2‐Substituted 2,3‐Dihydro‐3,3‐dimethyl‐1H‐isoindol‐1‐ones and 3,3‐Disubstituted (E)‐1‐(Arylimino)‐1,3‐dihydroisobenzofurans

A new and facile method for the preparation of 2‐substituted 2,3‐dihydro‐3,3‐dimethyl‐1H‐isoindol‐1‐ones 3 and 3,3‐disubstituted (E)‐1‐(arylimino)‐1,3‐dihydroisobenzofurans 6 has been developed. Thus, treatment of N‐alkyl(or aryl)‐2‐(1‐methylethen‐1‐yl)benzamides 2 with concentrated hydriodic acid (HI) in MeCN at room temperature afforded 3 . Similar treatment of N‐aryl‐2‐(1‐phenylethen‐1‐yl)benzamide 5 with concentrated HI at 0° afforded 6 .     

Copper-catalyzed Csp-chalcogen bond formation: Versatile approach to N-(3-(organochalcogenyl)prop-2-yn-1-yl)amides

This work describes the copper-catalyzed Csp-chalcogen bond formation through cross-coupling reactions of propynylbenzamides and diorganyl dichalcogenides at room temperature, under open atmosphere. Generally, the reactions have proceeded very smoothly, affording the new class of organochalcogen-containing propynylbenzamides in good yields. Notably, this protocol showed to be tolerant to neutral, electron-donating and electron-withdrawing substituents present in both reaction substrates. In addition, the applicability of the carbon-chalcogen bond as a reactive site has been proved by successfully employment of the N-methyl-N-(3-(butylselanyl)prop-2-yn-1-yl)benzamide as a precursor in palladium-catalyzed Suzuki and Sonogashira type reactions.