Rhodium/Silver-Cocatalyzed Transannulation of N-Sulfonyl-1,2,3-triazoles with Vinyl Azides: Divergent Synthesis of Pyrroles and 2 H-Pyrazines
- PMID: 27643511
- DOI: 10.1002/asia.201601164
Rhodium/Silver-Cocatalyzed Transannulation of N-Sulfonyl-1,2,3-triazoles with Vinyl Azides: Divergent Synthesis of Pyrroles and 2 H-Pyrazines
Abstract
The first cyclization reaction between vinyl azides and N-sulfonyl-1,2,3-triazoles is reported. A Rh/Ag binary metal catalyst system proved to be necessary for the successful cyclization. By varying the structure of vinyl azides, such reaction allows the divergent synthesis of pyrroles and 2H-pyrazines. The cyclization reactions feature a broad substrate scope, good functional group tolerance, high reaction efficiency, and good to high product yields.
Keywords: pyrazines; pyrroles; rhodium; silver; sulfonyl-1,2,3-triazoles; vinyl azides.
© 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Similar articles
-
Rhodium-catalyzed transannulation of 1,2,3-triazoles to polysubstituted pyrroles.J Org Chem. 2014 Sep 5;79(17):8428-34. doi: 10.1021/jo501043h. Epub 2014 Aug 11. J Org Chem. 2014. PMID: 25078729
-
One-pot synthesis of 2,5-dihydropyrroles from terminal alkynes, azides, and propargylic alcohols by relay actions of copper, rhodium, and gold.Chemistry. 2014 Dec 1;20(49):16078-82. doi: 10.1002/chem.201405357. Epub 2014 Oct 24. Chemistry. 2014. PMID: 25345587
-
Synthesis of pyrazines from rhodium-catalyzed reaction of 2H-Azirines with N-sulfonyl 1,2,3-triazoles.J Org Chem. 2015 Feb 20;80(4):2376-83. doi: 10.1021/acs.joc.5b00036. Epub 2015 Feb 2. J Org Chem. 2015. PMID: 25619593
-
Recent developments in the group-1B-metal-catalyzed synthesis of pyrroles.Org Biomol Chem. 2016 Jul 26;14(30):7136-49. doi: 10.1039/c6ob00962j. Org Biomol Chem. 2016. PMID: 27345290 Review.
-
[Reactions and syntheses of pyrazines].Yakugaku Zasshi. 1997 Jan;117(1):1-17. doi: 10.1248/yakushi1947.117.1_1. Yakugaku Zasshi. 1997. PMID: 9120799 Review. Japanese.
Cited by
-
Reductive radical-initiated 1,2-C migration assisted by an azidyl group.Chem Sci. 2020 Jul 7;11(30):7921-7926. doi: 10.1039/d0sc02559c. Chem Sci. 2020. PMID: 34123076 Free PMC article.
-
Modular Synthesis of Highly Substituted 3-Azapyrroles by Rh(II)-Catalyzed N-H Bond Insertion and Cyclodehydration.J Org Chem. 2022 Dec 16;87(24):16139-16156. doi: 10.1021/acs.joc.2c00434. Epub 2022 May 3. J Org Chem. 2022. PMID: 35503987 Free PMC article.
-
Vinylazides: versatile synthons and magical precursors for the construction of N-heterocycles.Mol Divers. 2021 Nov;25(4):2533-2570. doi: 10.1007/s11030-020-10106-1. Epub 2020 May 30. Mol Divers. 2021. PMID: 32474890 Review.
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
Other Literature Sources