Electrocyclizations of Conjugated Azapolyenes Produced in Reactions of Azaheterocycles with Metal Carbenes
Conjugated azapolyenes (azabuta-1,3-dienes, aza-/diaza-/oxaza-/oxadiazahexa-1,3,5-trienes) are highly reactive in electrocyclization reactions, which makes them convenient precursors for the synthesis of a wide range of four-, five-, and six-membered nitrogen heterocycles that are of relevance for m...
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doaj-84cfad7a99f545f3a333d1b47b5071252021-09-26T00:53:47ZengMDPI AGOrganics2673-401X2021-09-0121731333610.3390/org2030017Electrocyclizations of Conjugated Azapolyenes Produced in Reactions of Azaheterocycles with Metal CarbenesNikolai V. Rostovskii0Mikhail S. Novikov1Alexander F. Khlebnikov2Institute of Chemistry, St. Petersburg State University, 7/9 Universitetskaya Nab., 199034 Saint Petersburg, RussiaInstitute of Chemistry, St. Petersburg State University, 7/9 Universitetskaya Nab., 199034 Saint Petersburg, RussiaInstitute of Chemistry, St. Petersburg State University, 7/9 Universitetskaya Nab., 199034 Saint Petersburg, RussiaConjugated azapolyenes (azabuta-1,3-dienes, aza-/diaza-/oxaza-/oxadiazahexa-1,3,5-trienes) are highly reactive in electrocyclization reactions, which makes them convenient precursors for the synthesis of a wide range of four-, five-, and six-membered nitrogen heterocycles that are of relevance for medicinal chemistry. Ring opening reactions of 2<i>H</i>-azirines and azoles containing an N–N or N–O bond, initiated by a transition metal carbene, have become increasingly important in recent years, since they easily allow the generation of azapolyenes with different numbers of double bonds and heteroatoms in various positions. This review summarizes the literature, published mainly in the last decade, on the synthetic and mechanistic aspects of electrocyclizations of azapolyenes generated by the carbene method.https://www.mdpi.com/2673-401X/2/3/17electrocyclizationpericyclic reactionsazadienesrhodium carbenesisoxazolespyrazoles |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Nikolai V. Rostovskii Mikhail S. Novikov Alexander F. Khlebnikov |
spellingShingle |
Nikolai V. Rostovskii Mikhail S. Novikov Alexander F. Khlebnikov Electrocyclizations of Conjugated Azapolyenes Produced in Reactions of Azaheterocycles with Metal Carbenes Organics electrocyclization pericyclic reactions azadienes rhodium carbenes isoxazoles pyrazoles |
author_facet |
Nikolai V. Rostovskii Mikhail S. Novikov Alexander F. Khlebnikov |
author_sort |
Nikolai V. Rostovskii |
title |
Electrocyclizations of Conjugated Azapolyenes Produced in Reactions of Azaheterocycles with Metal Carbenes |
title_short |
Electrocyclizations of Conjugated Azapolyenes Produced in Reactions of Azaheterocycles with Metal Carbenes |
title_full |
Electrocyclizations of Conjugated Azapolyenes Produced in Reactions of Azaheterocycles with Metal Carbenes |
title_fullStr |
Electrocyclizations of Conjugated Azapolyenes Produced in Reactions of Azaheterocycles with Metal Carbenes |
title_full_unstemmed |
Electrocyclizations of Conjugated Azapolyenes Produced in Reactions of Azaheterocycles with Metal Carbenes |
title_sort |
electrocyclizations of conjugated azapolyenes produced in reactions of azaheterocycles with metal carbenes |
publisher |
MDPI AG |
series |
Organics |
issn |
2673-401X |
publishDate |
2021-09-01 |
description |
Conjugated azapolyenes (azabuta-1,3-dienes, aza-/diaza-/oxaza-/oxadiazahexa-1,3,5-trienes) are highly reactive in electrocyclization reactions, which makes them convenient precursors for the synthesis of a wide range of four-, five-, and six-membered nitrogen heterocycles that are of relevance for medicinal chemistry. Ring opening reactions of 2<i>H</i>-azirines and azoles containing an N–N or N–O bond, initiated by a transition metal carbene, have become increasingly important in recent years, since they easily allow the generation of azapolyenes with different numbers of double bonds and heteroatoms in various positions. This review summarizes the literature, published mainly in the last decade, on the synthetic and mechanistic aspects of electrocyclizations of azapolyenes generated by the carbene method. |
topic |
electrocyclization pericyclic reactions azadienes rhodium carbenes isoxazoles pyrazoles |
url |
https://www.mdpi.com/2673-401X/2/3/17 |
work_keys_str_mv |
AT nikolaivrostovskii electrocyclizationsofconjugatedazapolyenesproducedinreactionsofazaheterocycleswithmetalcarbenes AT mikhailsnovikov electrocyclizationsofconjugatedazapolyenesproducedinreactionsofazaheterocycleswithmetalcarbenes AT alexanderfkhlebnikov electrocyclizationsofconjugatedazapolyenesproducedinreactionsofazaheterocycleswithmetalcarbenes |
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1716869636115398656 |