Tetrabutylammonium fluoride promoted intramolecular nucleophilic attack of an ester group on a carbodiimide: Preparation of 1,3-oxazolin-5-ones and 3,1-benzoxazin-4-ones

Synthesis

Volumn , Issue 6, 1996, Pages 690-692

  Molina, P ^a   Aller, E ^a   Ecija M ^a   Lorenzo, A ^a  

^a UNIVERSITY OF MURCIA   (Spain)

Author keywords

azaheterocycles; carbodiimide; intramolecular nucleophilic attack; tetrabutylammonium fluoride

Indexed keywords

1,3 OXAZINE DERIVATIVE; 4H 3,1 BENZOXAZIN 4 ONE DERIVATIVE; OXAZOLINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0029813746     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-4284     Document Type: Article

References (11)

1. Khorana, H. G. Some Recent Developments in the Chemistry of Phosphate Esters of Biological Interest; Wiley: New York, 1961. Wünsch, E. Methoden der Organischen Chemie; Band 15: Synthese von Peptiden; G. Thieme Verlag: Stuttgart, 1974. Bodanszky, M.; Klausner, Y. S.; Ondety, M. Peptide Synthesis; Wiley: New York, 1976.
2. Khorana, H. G. Some Recent Developments in the Chemistry of Phosphate Esters of Biological Interest; Wiley: New York, 1961. Wünsch, E. Methoden der Organischen Chemie; Band 15: Synthese von Peptiden; G. Thieme Verlag: Stuttgart, 1974. Bodanszky, M.; Klausner, Y. S.; Ondety, M. Peptide Synthesis; Wiley: New York, 1976.
3. Khorana, H. G. Some Recent Developments in the Chemistry of Phosphate Esters of Biological Interest; Wiley: New York, 1961. Wünsch, E. Methoden der Organischen Chemie; Band 15: Synthese von Peptiden; G. Thieme Verlag: Stuttgart, 1974. Bodanszky, M.; Klausner, Y. S.; Ondety, M. Peptide Synthesis; Wiley: New York, 1976.
4. For a recent review, see: Molina, P.; Vilaplana, M. J. Synthesis 1994, 1197.
5. Wamhoff, H.; Muhr, J. Synthesis 1988, 919. Wamhoff, H.; Wintersohl, H.; Stölben, S.; Paasch, J.; Zhu, N-j, Z.; Gu, F. Liebigs Ann. Chem. 1990, 901.
6. Wamhoff, H.; Muhr, J. Synthesis 1988, 919. Wamhoff, H.; Wintersohl, H.; Stölben, S.; Paasch, J.; Zhu, N-j, Z.; Gu, F. Liebigs Ann. Chem. 1990, 901.
7. Molina, P.; Tárraga, A.; Espinosa, A. Synthesis 1989, 923.
8. Molina, P.; Tárraga, A.; Lidón, M. J. J. Chem. Soc., Perkin Trans 1 1990, 1727.
9. Molina, P.; Aller, E.; López-Lázaro, A.; Alajarin, M.; Lorenzo, A. Tetrahedron Lett. 1994, 3817.
10. Molina, P.; Fresneda, P. M.; Hurtado, F. Synth. Commun. 1987, 17, 485. Wamhoff, H.; Herrmann, S.; Stölben, S.; Nieger, M. Tetrahedron 1993, 49, 581.
11. Molina, P.; Fresneda, P. M.; Hurtado, F. Synth. Commun. 1987, 17, 485. Wamhoff, H.; Herrmann, S.; Stölben, S.; Nieger, M. Tetrahedron 1993, 49, 581.