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首页> 外文期刊>Acta crystallographica. Section C, Structural chemistry. >Five closely related 4-chloro-6,11-dihydro-5H-benzo[b]pyrimido[5,4-f]azepines: similar molecular structures but different supramolecular assemblies
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Five closely related 4-chloro-6,11-dihydro-5H-benzo[b]pyrimido[5,4-f]azepines: similar molecular structures but different supramolecular assemblies

机译：五个密切相关的4-氯-6,11-二氢-5H-苯并[b]嘧啶并[5,4-f] a庚因：相似的分子结构但不同的超分子组装体

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摘要

Dibenz[b,f]azepine (DBA) is a privileged 6-7-6 tricyclic ring system of importance in both organic and medicinal chemistry. Benzo[b]pyrimido[5,4-f]azepines (BPAs), which also contain a privileged 6-7-6 ring system, are less well investigated, probably because of a lack of straightforward and versatile methods for their synthesis. A simple and versatile synthetic approach to BPAs based on intramolecular Friedel–Crafts alkylation has been developed. A group of closely-related benzo[b]pyrimido[5,4-f]azepine derivatives, namely (6RS)-4-chloro-6,11-dimethyl-6,11-dihydro-5H-benzo[b]pyrimido[5,4-f]azepine, C14H14ClN3, (I), (6RS)-4-chloro-8-hydroxy-6,11-dimethyl-6,11-dihydro-5H-benzo[b]pyrimido[5,4-f]azepine, C14H14ClN3O, (II), (6RS)-4-chloro-8-methoxy-6,11-dimethyl-6,11-dihydro-5H-benzo[b]pyrimido[5,4-f]azepine, C15H16ClN3O, (III), and (6RS)-4-chloro-8-methoxy-6,11-dimethyl-2-phenyl-6,11-dihydro-5H-benzo[b]pyrimido[5,4-f]azepine, C21H20ClN3O, (IV), has been prepared and their structures compared with the recently published structure [Acosta-Quintero et al. (2015). Eur. J. Org. Chem. pp. 5360–5369] of (6RS)-4-chloro-2,6,8,11-tetramethyl-6,11-dihydro-5H-benzo[b]pyrimido[5,4-f]azepine, (V). All five compounds crystallize as racemic mixtures and they have very similar molecular conformations, with the azepine ring adopting a boat-type conformation in each case, although the orientation of the methoxy substituent in each of (III) and (IV) is different. The supramolecular assemblies in (II) and (IV) depend upon hydrogen bonds of the O—H...N and C—H...π(arene) types, respectively, those in (I) and (V) depend upon π–π stacking interactions involving pairs of pyrimidine rings, and that in (III) depends upon a π–π stacking interaction involving pairs of phenyl rings. Short C—Cl...π(pyrimidine) contacts are present in (I), (II) and (IV) but not in (III) or (V).
机译：Dibenz [b，f] azepine（DBA）是特权的6-7-6三环系统，在有机化学和药物化学中均具有重要意义。苯并[b]嘧啶并[5,4-f]氮杂（BPA），也包含特权的6-7-6环系统，研究较少，可能是由于缺乏简单而通用的合成方法。已经开发了一种基于分子内Friedel-Crafts烷基化的BPA的简单通用合成方法。一组密切相关的苯并[b]嘧啶并[5,4-f] a庚因衍生物，即（6RS）-4-氯-6,11-二甲基-6,11-二氢-5H-苯并[b]嘧啶并[ 5,4-f] a庚因，C14H14ClN3，（I），（6RS）-4-氯-8-羟基-6,11-二甲基-6,11-二氢-5H-苯并[b]嘧啶基[5,4- f]氮杂，C14H14ClN3O，（II），（6RS）-4-<！tlsb = -0.14pt>氯-8-甲氧基-6,11-二甲基-6,11-二氢-5H-苯并[b]嘧啶基[5,4-f]氮杂，C15H16ClN3O，（III）和（6RS）-4-氯-8-甲氧基-6,11-二甲基-2-苯基-6,11-二氢-5H-苯并[b]制备了嘧啶并[5,4-f]氮杂环庚烷C21H20ClN3O（IV），并将其结构与最近发表的结构进行比较[Acosta-Quintero等人。 （2015）。欧元。 J.组织化学第（6RS）-4-氯-2,6,8,11-四甲基-6,11-二氢-5H-苯并[b]嘧啶[5,4-f]氮杂（5RS）第pp。5360–5369] 。所有五种化合物均以外消旋混合物的形式结晶，并且它们具有非常相似的分子构象，尽管（III）和（IV）各自的甲氧基取代基的取向不同，但氮杂环均采用船型构象。 （II）和（IV）中的超分子组装体分别取决于OH ... N和CH ...π（芳烃）类型的氢键，（I）和（V）中的超分子组装体取决于涉及嘧啶环对的π-π堆积相互作用，而（III）中的相互作用取决于涉及苯环对的π-π堆积相互作用。在（I），（II）和（IV）中存在短的CCl ...π（嘧啶）触点，但在（III）或（V）中不存在。

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