Efficient solvent-free synthesis of benzothiazine-fused pyrrolo[3,4-c]coumarins: Cycloaddition reactions between coumarin-based dihydrobenzothiazoles and isocyanides

Helvetica Chimica Acta

Volumn 97, Issue 6, 2014, Pages 847-853

  Khoobi, Mehdi ^a,b   Ramazani, Ali ^c   Mahdavi, Mohammad ^d   Foroumadi, Alireza ^a   Emami, Saeed ^b   Joo, Sang Woo ^e   Ślepokura, Katarzyna ^f   Lis, Tadeusz ^f   Shafiee, Abbas ^d  

^a TEHRAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^b MAZANDARAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^c UNIVERSITY OF ZANJAN   (Iran)

^d TEHRAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^e Yeungnam University   (South Korea)

^f UNIVERSITY OF WROC AW   (Poland)

Author keywords

Benzothiazoles, 2,3 dihydro ; Coumarins; Cycloadditions; Isocyanides

Indexed keywords

CYCLOADDITION;

BENZOTHIAZOLES; COUMARINS; CYCLOADDITION REACTION; CYCLOADDITIONS; ISOCYANIDES; SOLVENT FREE CONDITIONS; SOLVENT FREE SYNTHESIS; TITLE COMPOUNDS;

CYANIDES;

14 (CYCLOHEXYLAMINO) 4 METHOXY[1]BENZOPYRANO[3',4':3,4]PYRROLO[2,1 C][1,4]BENZOTHIAZIN 6(7H) ONE; 14 (CYCLOHEXYLAMINO)[1]BENZOPYRANO[3',4':3,4]PYRROLO[2,1 C][1,4]BENZOTHIAZIN 6(7H) ONE; 14 [(1,1,3,3 TETRAMETHYLBUTYL)AMINO][1]BENZOPYRANO[3',4':3,4]PYRROLO[2,1 C][1,4]BENZOTHIAZIN 6(7H) ONE; 14 [(TERT BUTYL)AMINO] 4 METHOXY [1]BENZOPYRANO[3',4':3,4]PYRROLO[2,1 C][1,4]BENZOTHIAZIN 6(7H) ONE; 14 [(TERT BUTYL)AMINO][1]BENZOPYRANO[3',4':3,4]PYRROLO[2,1 C][1,4]BENZOTHIAZIN 6(7H) ONE; 2 BROMO 14 (CYCLOHEXYLAMINO)[1]BENZOPYRANO[3',4':3,4]PYRROLO[2,1 C][1,4]BENZOTHIAZIN 6(7H) ONE; 2 BROMO 14 [(1,1,3,3 TETRAMETHYLBUTYL)AMINO][1]BENZOPYRANO[3',4':3,4]PYRROLO[2,1 C][1,4]BENZOTHIAZIN 6(7H) ONE; 4 METHOXY 14 [(1,1,3,3 TETRAMETHYLBUTYL)AMINO][1]BENZOPYRANO[3',4':3,4]PYRROLO[2,1 C][1,4]BENZOTHIAZIN 6(7H) ONE; BENZOTHIAZINE DERIVATIVE; BENZOTHIAZINE FUSED PYRROLO[3,4 C]COUMARIN; BENZOTHIAZOLE DERIVATIVE; COUMARIN DERIVATIVE; CYANIDE; DIHYDROBENZOTHIAZOLE; ISOCYANIDE; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; CRYSTAL STRUCTURE; CYCLOADDITION; DRUG SYNTHESIS; HEATING; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS; RING OPENING; TAUTOMERIZATION; X RAY CRYSTALLOGRAPHY;

EID: 84902491150     PISSN: 0018019X     EISSN: 15222675     Source Type: Journal    
DOI: 10.1002/hlca.201300310     Document Type: Article

References (30)

1. M. Oshita, K. Yamashita, M. Tobisu, N. Chatani, J. Am. Chem. Soc. 2005, 127, 761
2. N. Obata, T. Takizawa, Tetrahedron Lett. 1969, 10, 3403
3. Y. Ito, H. Kato, T. Saegusa, J. Org. Chem. 1982, 47, 741
4. J. H. Rigby, M. N. Qabar, J. Am. Chem. Soc. 1991, 113, 8975
5. G. Kollenz, W. Ott, E. Ziegler, K. Peters, H. G. v. Schnering, H. Quast, Liebigs Ann. Chem. 1980, 1801
6. W. Ott, C. Kratky, P. Seiler, Liebigs Ann. Chem. 1980, 1711
7. J. Moskal, A. M. van Leusen, J. Org. Chem. 1986, 51, 4131.
8. M. Quai, S. Frattini, U. Vendrame, M. Mondoni, S. Dossena, E. Cereda, Tetrahedron Lett. 2004, 45, 1413.
9. V. Nair, R. S. Menon, A. U. Vinod, S. Viji, Tetrahedron Lett. 2002, 43, 2293.
10. M. Strzelczyk, H. Matyjewska, H. Strozynski, Pol. J. Pharmacol. Pharm. 1990, 42, 377
11. I. Kostova, Curr. Med. Chem. Anti-Cancer Agents 2005, 5, 29
12. K. C. Fylaktakidou, D. J. Hadjipavlou-Litina, K. E. Litinas, D. N. Nicolaides, Curr. Pharm. Des. 2004, 10, 3813.
13. R. G. Harvey, C. Cortez, T. P. Ananthanarayan, S. Schmolka, J. Org. Chem. 1988, 53, 3936.
14. Q. Li, J. Jiang, A. Fan, Y. Cui, Y. Jia, Org. Lett. 2011, 13, 312
15. H. Fan, J. Peng, M. T. Hamann, J. Hu, Chem. Rev. 2008, 108, 264
16. D. Pla, F. Albericio, M. Álvarez, Anti-Cancer Agents Med. Chem. 2008, 8, 746
17. S. T. Handy, Y. Zhang, Org. Prep. Proced. Int. 2005, 37, 411
18. C. Bailly, Curr. Med. Chem. Anti-Cancer Agents 2004, 4, 363.
19. D. Pla, A. Marchal, C. A. Olsen, A. Francesch, C. Cuevas, F. Albericio, M. Alvarez, J. Med. Chem. 2006, 49, 3257.
20. M. Khoobi, A. Foroumadi, S. Emami, M. Safavi, G. Dehghan, B. H. Alizadeh, A. Ramazani, S. K. Ardestani, A. Shafiee, Chem. Biol. Drug Des. 2011, 78, 580.
21. M. Khoobi, S. Emami, G. Dehghan, A. Foroumadi, A. Ramazani, A. Shafiee, Arch. Pharm. 2011, 344, 588
22. M. R. Ganjali, S. Aghabalazadeh, M. Khoobi, A. Ramazani, A. Foroumadi, A. Shafiee, P. Norouzi, Int. J. Electrochem. Sci. 2011, 6, 52.
23. S. H. Mashraqui, R. M. Kellogg, Tetrahedron Lett. 1985, 26, 1457.
24. A. Dömling, Chem. Rev. 2006, 106, 17
25. A. Dömling, I. Ugi, Angew. Chem., Int. Ed. 2000, 39, 3169
26. I. Ugi, 'Isonitrile Chemistry', Academic, London, 1971
27. I. Ugi, Angew. Chem., Int. Ed. 1982, 21, 810
28. H. M. Walborsky, M. P. Periasamy, 'The Chemistry of Functional Groups, Supplement C', Eds. S. Patai, Z. Rappaport, Wiley, New York, NY, 1983, Chapt. 8.20, pp. 835-837
29. V. Nair, A. U. Vinod, J. S. Nair, A. R. Sreekanth, N. P. Rath, Tetrahedron Lett. 2000, 41, 6675.
30. G. M. Sheldrick, Acta Crystallogr., Sect. A 2008, 64, 112.