Rapid and efficient synthesis of 2-amino-4H-benzothiazines

Organic Letters

Volumn 2, Issue 23, 2000, Pages 3667-3670

  Hari, Anitha ^a   Miller, Benjamin L ^a  

^a UNIVERSITY OF ROCHESTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000073952     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006580m     Document Type: Article

References (14)

1. For recent reviews of heterocycle synthesis, see: (a) Nefzi, A.; Ostresh, J. M.; Houghten, R. A. Chem. Rev. 1997, 97, 449-472.
2. (b) Franzén, R. G. J. Comb. Chem. 2000, 2, 195-214.
3. For syntheses of 4-aryl and unsubstituted 4H-3,1-benzothiazines, see: (a) Nishio, T. J. Org. Chem. 1997, 62, 1106-1111.
4. (b) El-Desoky, S. I.; Kandeel, E. M.; Abd-el-Rahman, A. H.; Schmidt, R. R. J. Herocycl.Chem. 1999, 36, 153-160.
5. (a) Hari, A.; Miller, B. L. Angew. Chem., Int. Ed. Engl. 1999, 38, 2777-2779.
6. (b) Hari, A.; Miller, B. L. Org. Lett. 2000, 2, 691-693.
7. Wang, S. J. Am. Chem. Soc. 1973, 95, 1328-1333.
8. Rink, H. Tetrahedron Lett. 1987, 28, 3787-3790.
9. 2O) provided the desired benzothiazine essentially pure as a white solid (14 mg, 65%).
10. 2H) was performed over 30 min at a flow rate of 300 μL/min.
11. Xin, Z.; Pei, Z.; von Geldem, T.; Jirousek, M. Tetrahedron Lett. 2000, 41, 1147-1150.
12. Tárraga, A.; Molina, P.; López, J. L. Tetrahedron Lett. 2000, 41, 4895-4899.
13. For alternative solid-supported preparations of ureas, see: (a) Gordeev, M. F.; Hui, H. C.; Gordon, E. M.; Patel, D. V. Tetrahedron Lett. 1997, 38, 1729-1732.
14. (b) Wang, G. T.; Chen, Y.; Wang, S.; Sciotti, R.; Sowin, T. Tetrahedron Lett. 1997, 38, 1895-1898.