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Synthesis 2021; 53(11): 1911-1922
DOI: 10.1055/s-0040-1706006
DOI: 10.1055/s-0040-1706006
paper
Sequencing Groebke–Blackburn–Bienaymé and Aza-Michael Addition Reactions: A Modular Strategy for Accessing a Diverse Collection of Constrained Benzoxazepine and Imidazopyrazine Systems
This work was supported by generous grants from the Islamic Development Bank (IsDB), Transform Fund (Grant No. 2018-2021) and the Research Funding Department, University of Sharjah, UAE (Grant No. 1801110125-P).
Abstract
We present a divergent strategy that permits access to diversely functionalized benzoxazepinium scaffolds fused to various heterocycles. The described strategy features a one-pot combination of the Groebke–Blackburn–Bienaymé reaction and an aza-Michael addition. Methyl (E)-4-(2-formylphenoxy)but-2-enoate and its derivatives are utilized as central elements in this cascade. These building blocks are reacted with a variety of functionalized amino-azines and tert-butyl isocyanide under ytterbium triflate [Yb(OTf)3] catalysis. The ensuing cascade represents a rapid, modular and atom-economic process that leads to the construction of a diverse collection of constrained benzoxazepinium systems from a wide substrate scope.
Key words
aza-Michael addition - benzoxazepines - indolopyrazines - diversity-oriented synthesis - multicomponent reactions - Groebke–Blackburn–Bienaymé - modular synthesisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706006.
- Supporting Information
Publication History
Received: 01 October 2020
Accepted after revision: 07 December 2020
Article published online:
07 January 2021
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