Advances in Organic Synthesis

Volume: 9

Synthesis of N,O,S-Heterocycles by One-Pot Reactions of Epoxides, Aziridines and Oxaziridines

Author(s): Oleksandr Zhurakovskyi and Vitalii Palchykov

Pp: 147-248 (102)

DOI: 10.2174/9781681086958118090007

* (Excluding Mailing and Handling)


Discovery of new effective methods for the synthesis of aziridines, epoxides and oxaziridines, as well as development of novel transformations of these heterocycles, has been an extremely active area of research in recent years. In just two or three steps, these small heterocycles can be converted into a vast array of four-toseven- membered rings and open-chain compounds. The diversity of possible transformations transpired in a torrent of publications, with hundreds of papers published every year. This review covers recent (2007 to the end of 2017) literature on one-pot transformations of aziridines, epoxides, and oxaziridines. Within this, deceptively narrow, topic there is a great number of synthetically useful or mechanistically interesting reactions leading to diverse families of N,O,S-heterocycles, including thiiranes, oxetanes, azetidines, azetidinones, furans, 1,3-oxazolines, 1,3- oxazolidines, 1,3-oxazolidin-2-ones, 1,3-thiazolidines, imidazoles, 1,2,3-triazoles, pyrans, 1,4-oxazines (morpholines), azepanes, oxazepanes etc. The review aims to give the readers an insight into the great practical utility of epoxides, aziridines and oxaziridines. It presents the most modern methods for their expedited conversion into a broad range of heterocycles.

Keywords: Aziridines, Azetidines, Azetidinones, Azepanes, Cycloaddition, Epoxides, Furans, Imidazoles, Isomerization, N, O, S-heterocycles, Oxaziridines, Oxetanes, Oxazepanes, 1, 3-Oxazolines, 1, 3-Oxazolidines, 1, 3-Oxazolidin-2-ones, 1, 4-Oxazines (morpholines), Pyrans, Pyrrolidines, Pyrroles, Rearrangement, Ring expansion, Ring-opening reaction, Thiiranes, Transition-metal catalysis, 1, 3- Thiazolidines, 1, 2, 3-Triazoles.

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