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Solid acid-catalyzed domino cyclization reaction: regio- and diastereoselective synthesis of pyrido[2,3-d]pyrimidine derivatives bearing three contiguous stereocenters.
- Source :
-
Green Chemistry . 5/7/2018, Vol. 20 Issue 9, p2057-2063. 7p. - Publication Year :
- 2018
-
Abstract
- An efficient and green domino approach for the synthesis of 5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-4(3H)-one derivatives using a recoverable carbonaceous material as a catalyst has been established. The new domino reaction was conducted by reacting the readily available and inexpensive starting materials 2,6-diaminopyrimidin-4(3H)-one, nitroolefin and aldehyde in water. A total of 24 examples were examined, and showed a broad substrate scope and high yields. The carbonaceous material catalyst can be reused at least 5 times without obvious deactivation. The proposed mechanism has explained the reaction process and the resulting high regio- and diastereoselectivities. The present green strategy shows attractive characteristics such as using water as a green medium, using an inexpensive and recoverable solid acid catalyst, and having a simple work-up/purification, without generating any waste products or using any metal promoters. [ABSTRACT FROM AUTHOR]
- Subjects :
- *RING formation (Chemistry)
*PYRIMIDINE derivatives
Subjects
Details
- Language :
- English
- ISSN :
- 14639262
- Volume :
- 20
- Issue :
- 9
- Database :
- Academic Search Index
- Journal :
- Green Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 129526631
- Full Text :
- https://doi.org/10.1039/c7gc03812g