Abstract

A concise, efficient, and versatile approach to access novel tetrahydro-1H-benzo[b]azepine-2-carboxylic acids and tricyclic tetra­hydro-1-benzazepines carrying [a]-fused heterocyclic units is reported. The easily accessible 2-(allylaryl)glycinates were used as starting material to synthesize, via the corresponding 1,4-epoxycycloadducts, the required key intermediate benzo[b]azepine-2-carboxylates. Hydrolysis of the latter afforded the targeted benzo[b]azepine-2-carboxylic acids. The key intermediate was also converted into N-2-chloroacetyl derivatives which, in turn, were transformed into the corresponding tricyclic target hexahydrobenzo[f]pyrazino[1,2-a]azepine-1,4-diones by reaction with benzylamine or aminoethanol. The reaction of the common intermediate with hydrazine gave the corresponding intermediate carbohydrazides, which, by reaction with trimethoxymethane, were transformed into another tricyclic target tetrahydrobenzo[f][1,2,4]tri­azino[4,5-a]azepin-4(3H)-ones. Full spectroscopic characterization (IR, HRMS, and ¹H and ¹³C NMR) is also reported for each compound.

Publication History

Received: 19 July 2020

Accepted after revision: 07 September 2020

Publication Date:
15 October 2020 (online)

© 2020. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

中文翻译：

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容易获得带有[a]-稠合2-（烯丙基芳基）甘氨酸盐杂环单元的新型四氢-1-苯并enza庚因-2-羧酸和四氢-1-苯并ze庚因

摘要

据报道，一种简洁，有效且通用的方法可访问带有[ a ]稠合杂环单元的新型四氢-1 H-苯并[ b ]氮杂-2-羧酸和三环四氢-1-苯并氮杂。易于获得的2-（烯丙基芳基）甘氨酸盐用作起始原料，通过相应的1，4-环氧环加合物合成所需的关键中间体苯并[ b ]氮杂-2-羧酸酯。后者的水解得到目标苯并[ b ]氮杂-2-羧酸。关键中间体也被转化为N -2-氯乙酰基衍生物，然后依次转化为相应的三环目标六氢苯并[ f ]吡嗪并[1,2-通过与苄胺或氨基乙醇反应生成]] azepine-1,4-二酮。普通中间体与肼的反应产生了相应的中间体碳酰肼，该中间体碳酰肼通过与三甲氧基甲烷反应转化为另一种三环目标四氢苯并[ f ] [1,2,4]三嗪[4,5 - a ] azepin-4（ 3 H）-一个。还报道了每种化合物的全光谱表征（IR，HRMS，¹ H和¹³ C NMR）。

出版历史

收到：2020年7月19日

修订后接受：2020年9月7日

发布日期：
2020年10月15日（在线）

©2020年。Thieme。版权所有

Georg Thieme Verlag
KGRüdigerstraße14，70469斯图加特，德国