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Synthesis 2016; 48(02): 238-244
DOI: 10.1055/s-0035-1560809
DOI: 10.1055/s-0035-1560809
paper
Synthesis of Benzotriazepine Derivatives via [4+3] Cycloaddition of Aza-o-quinone Methide Intermediates and Azomethine Imines
Further Information
Publication History
Received: 02 October 2015
Accepted: 05 October 2015
Publication Date:
05 November 2015 (online)
![](https://www.thieme-connect.de/media/synthesis/201602/lookinside/thumbnails/ss-2015-z0578-op_10-1055_s-0035-1560809-1.jpg)
Abstract
An efficient and unprecedented [4+3] cycloaddition between in situ generated aza-o-quinone methides and azomethine imines via an aza-Michael/aminalization sequence has been developed. The scalable protocol allows to expeditiously assemble a valuable heterocyclic system incorporating tetrahydroisoquinoline and benzotriazepine scaffolds in good to excellent yields under mild conditions.
Key words
[4+3] cycloaddition - aza-o-quinone methide - azomethine imine - triazepine - 7-membered heterocyclesSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1560809.
- Supporting Information
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For reviews on o-quinone methides, see:
For an excellent review, see:
For selected examples, see: