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- Title
Syntheses of 2-Unsubstituted 1 H-1,3-Benzazaphospholes from N-Formyl-2-bromoanilides.
- Authors
Ghalib, Mohammed; Niaz, Basit; Jones, Peter G.; Heinicke, Joachim W.
- Abstract
ABSTRACT The phosphonylation of 2-bromo-formylanilides 1 with triethyl phosphite in the presence of preformed Pd(0)(triethyl phosphite)n catalyst furnished 2-phosphono-formanilides 2 in good yields. Reduction with excess LiAlH4 provided mainly N-methyl-2-phosphinoanilines 3 and minor amounts of 1,2-unsubstituted benzazaphospholes 4. N-Methyl-1,3-benzazaphospholes 5 were synthesized by the cyclocondensation of 3 with dimethylformamide dimethylacetal (DMFA). A more convenient route to 5, avoiding the chromatographic separation of 4, is the reduction of 1 to 2-bromo-N-methylaniline 6, followed by phosphonylation to 7, LiAlH4 reduction, and cyclization with DMFA. The coordination properties at σ2P of benzazaphospholes are characterized by structural data obtained by the crystal structure analysis of ( 5b)W(CO)5.
- Subjects
CATALYSTS; CHEMICAL inhibitors; DIMETHYLFORMAMIDE; HETEROCYCLIC compounds; PHOSPHORINE
- Publication
Heteroatom Chemistry, 2013, Vol 24, Issue 6, p452
- ISSN
1042-7163
- Publication type
Article
- DOI
10.1002/hc.21111