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Synthesis 2021; 53(07): 1315-1330
DOI: 10.1055/s-0040-1706484
DOI: 10.1055/s-0040-1706484
paper
Easy Access to Novel Tetrahydro-1-benzazepine-2-carboxylic Acids and Tetrahydro-1-benzazepines Carrying [a]-Fused Heterocyclic Units from 2-(Allylaryl)glycinates
A.P. would like to thank Vicerrectoría de Investigación y Extensión of the Industrial University of Santander (Grant No. 2496) for financial support.
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.
Key words
2-(allylaryl)glycinates - intramolecular 1,3-dipolar cycloaddition - reductive cleavage - cyclocondensation - tricyclic fused-[a]-1-benzazepinesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706484.
- Supporting Information
Publication History
Received: 19 July 2020
Accepted after revision: 07 September 2020
Article published online:
15 October 2020
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