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Synthesis 2015; 47(18): 2781-2790
DOI: 10.1055/s-0034-1378717
DOI: 10.1055/s-0034-1378717
special topic
Synthesis and Reactivity of Aziridines with Internal Dipolarophiles: An Approach to 1,4-Dihydrochromeno[4,3-b]pyrroles and 3-Methylenechromano[4,3-b]pyrroles
Weitere Informationen
Publikationsverlauf
Received: 09. April 2015
Accepted after revision: 01. Mai 2015
Publikationsdatum:
24. Juni 2015 (online)
![](https://www.thieme-connect.de/media/synthesis/201518/lookinside/thumbnails/ss-2015-c0235-st_10-1055_s-0034-1378717-1.jpg)
Abstract
Aziridines derived from 2-(prop-2-yn-1-yloxy)- and 2-(buta-2,3-dien-1-yloxy)chalcones and from benzyl 2-(prop-2-yn-1-yloxy)- and 2-(buta-2,3-dien-1-yloxy)phenylacrylates were prepared in a stereoselective fashion. Their reactivity as azomethine ylide precursors was examined, leading to the synthesis of 1,4-dihydrochromeno[4,3-b]pyrrole and 3-methylenechromano[4,3-b]pyrrole derivatives through intramolecular 1,3-dipolar cycloaddition reactions.
Key words
polycycles - heterocycles - allenes - alkynes - cycloadditions - ylides - pyrroles - chromenesSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1378717.
- Supporting Information
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