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Rhodium-catalysed synthesis of fused pyrimidine derivatives employing N-sulfonyl-1,2,3-triazoles as a 1-aza-[4C] synthon.
- Source :
-
Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry . Jul2019, Vol. 60 Issue 28, p1849-1853. 5p. - Publication Year :
- 2019
-
Abstract
- • N -sulfonyl-1,2,3-triazole was used as a 1-aza-[4C] synthon. • Excellent chemoselectivity was observed. • Fused pyrimidine and seven-membered 1 H -1,4-diazepine were synthesized effectively. A new synthetic application of N -sulfonyl-1,2,3-triazoles acting as a 1-aza-[4C] synthon via the 1,2-shift reaction of an α-imine rhodium carbene was developed for the synthesis of fused pyrimidine derivatives. The high reactivity of the strained three-membered 2 H -azirine ring facilitated the unusual cyclization of electron-deficient dienes with electron-deficient dienophiles. The compatibility was good with common functionalities tolerated. Excellent chemoselectivity was observed, and no reactions occurred between the rhodium carbene and 2 H -azirine. The products could be converted into seven-membered multi-functionalized 1 H -1,4-diazepine derivatives, illustrating the potential application of the protocol in medium-sized N -heterocycle synthesis. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00404039
- Volume :
- 60
- Issue :
- 28
- Database :
- Academic Search Index
- Journal :
- Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 137209970
- Full Text :
- https://doi.org/10.1016/j.tetlet.2019.06.023