One-pot synthesis of 2,3-disubstituted N-tosylindoles from o-acyl-N-tosylanilines

Synthesis

Volumn , Issue 8, 2006, Pages 1249-1252

  Hari, Yoshiyuki ^a   Kanie, Tomoki ^a   Miyagi, Takashi ^a   Aoyama, Toyohiko ^a  

^a NAGOYA CITY UNIVERSITY   (Japan)

Author keywords

Alkylidenecarbene; Indoles; Lithium trimethylsilyldiazomethane; o acylanilines; One pot synthesis

Indexed keywords

ALKYLATION; LITHIUM COMPOUNDS;

ALKYLIDENECARBENE; INDOLES; LITHIUM TRIMETHYLSILYLDIAZOMETHANE; O-ACYLANILINES; ONE-POT SYNTHESIS;

SYNTHESIS (CHEMICAL);

2 ACYL N TOSYLANILINE DERIVATIVE; 2,3 N TOSYLINDOLE DERIVATIVE; ANILINE DERIVATIVE; INDOLE DERIVATIVE; LITHIUM TRIMETHYLSILYLDIAZOMETHANE; METHANE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; MEDICAL RESEARCH; SYNTHESIS;

EID: 33646270204     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-926398     Document Type: Article

References (12)

1. For reviews, see: (a) Pindur, U.; Adam, R. J. Heterocycl. Chem. 1988, 25, 1.
2. (b) Gribble, G. W. J. Chem. Soc., Perkin Trans, 1 2000, 1045.
3. Miyagi, T.; Hari, Y.; Aoyama, T. Tetrahedron Lett. 2004, 45, 6303.
4. Collins, M. A.; Tanis, S. P. Encyclopedia of Reagents for Organic Synthesis, Vol. 5; Paquette, L. A., Ed.; John Wiley & Sons: Chichester. 1995, 2992.
5. 10
6. When the synthesis of 5a from 2a was carried out by standard step-wise procedure, the overall yield of 5a was ca. 70%.
7. Ames, D. E. J. Chem. Soc. 1964, 1763.
8. Fryer, R. I.; Winter, D.; Sternbach, L. H. J. Heterocycl. Chem. 1967, 4, 355.
9. Goujon, J.-Y. G.; Zammattio, F.; Chrétien, J.-M.; Beaudet, I. Tetrahedron 2004, 60, 4037.
10. (a) Kikugawa, Y. Synthesis 1981, 461.
11. (b) Yamane, M.; Kubota, Y.; Narasaka, K. Bull. Chem. Soc. Jpn. 2005, 78, 331.
12. Jones, C. D. J. Org. Chem. 1972, 37, 3624.