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A selective synthesis of enamines versus aziridines.
- Source :
-
Journal of Heterocyclic Chemistry . Jan2011, Vol. 48 Issue 1, p129-134. 6p. 5 Diagrams, 1 Chart. - Publication Year :
- 2011
-
Abstract
- The reaction of 10-azidoacetyl-10 H-phenothiazine with olefinic dipolarophiles depends on the reaction temperature. In refluxing toluene, a mixture of enamine and aziridine is formed in 3:1 ratio. The reaction mechanism appears to involve a Michael-type addition of the nucleophilic N azide atom to the olefinic double bond. In chloroform, a cycloaddition reaction takes place with the formation of a 4,5-dihydro-1,2,3-triazole. The heating of dihydrotriazoles in toluene is accompanied by nitrogen elimination leading to a mixture of enamine and aziridine in 1:3 ratio. J. Heterocyclic Chem., 2011. [ABSTRACT FROM AUTHOR]
- Subjects :
- *ENAMINES
*AZIRIDINES
*PHENOTHIAZINE
*TOLUENE
*NUCLEOPHILIC reactions
Subjects
Details
- Language :
- English
- ISSN :
- 0022152X
- Volume :
- 48
- Issue :
- 1
- Database :
- Academic Search Index
- Journal :
- Journal of Heterocyclic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 57509526
- Full Text :
- https://doi.org/10.1002/jhet.529