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Synthesis 2015; 47(17): 2593-2598
DOI: 10.1055/s-0034-1379932
DOI: 10.1055/s-0034-1379932
paper
Synthesis of Tricyclic 1,2,3-Triazolopyridines
Further Information
Publication History
Received: 06 March 2015
Accepted after revision: 28 April 2015
Publication Date:
24 June 2015 (online)
Abstract
Novel tricyclic triazolopyridines were prepared in two steps from the requisite bicyclic 2-ketopyridines. In order to examine the scope of the process, a reliable route to the 2,3-dihydro-1,5-naphthyridin-4(1H)-one, 7,8-dihydro-5H-pyrido[3,2-b]azepin-9(6H)-one, 7,8-dihydrooxepino[3,2-b]pyridin-9(6H)-one, and 7,8-dihydro-5H-pyrido[3,2-c]azepin-9(6H)-one scaffolds was also established.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1379932.
- Supporting Information
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References
- 1a Jones G, Sliskovic DR. Tetrahedron Lett. 1980; 21: 4529
- 1b Jones G, Mouat DJ, Tonkinson DJ. J. Chem. Soc., Perkin Trans. 1 1985; 2719
- 1c Liu S, Sawicki J, Driver TG. Org. Lett. 2012; 14: 3744
- 2a Shi Y, Gulevich AV, Gevorgyan V. Angew. Chem. Int. Ed. 2014; 53: 14191
- 2b Chiassai L, Adam R, Drechslerová M, Ballesteros R, Abarca B. J. Fluorine Chem. 2014; 164: 44
- 3 Helan V, Gulevich AV, Gevorgyan V. Chem. Sci. 2015; 6: 1928
- 4 Adam R, Bilbao-Ramos P, López-Molina S, Abarca B, Ballesteros R, González-Rosende ME, Dea-Ayuela MA, Alzuet-Piña G. Bioorg. Med. Chem. 2014; 22: 4018
- 5a Using MnO2: Zimmerman HE, Ignatchenko A. J. Org. Chem. 1999; 64: 6635
- 5b Hirayama T, Ueda S, Okada T, Tsurue N, Okuda K, Nagasawa H. Chem. Eur. J. 2014; Catalytic: 20: 4156
- 6 Tran TP, Patel N, Samas B, Schwarz JB. Org. Biomol. Chem. 2009; 7: 5063
- 7 Mosher WA, El-Zimaity T, Lipp DW. J. Org. Chem. 1971; 36: 3890
- 8 Prophetic syntheses of N-Boc 10, N-Boc 13, and 17 were previously described: Biswas K, Brown J, Chen JJ, Gore VK, Harried S, Horne DB, Kaller MR, Ma VV, Nguyen TT, Sham K, Zhong W. PCT Int. Appl WO 2014025651 A1, 2014 ; Chem. Abstr. 2014, 160, 326771.
- 9 Frischmuth A, Knochel P. Angew. Chem. Int. Ed. 2013; 52: 10084