Facile assembly of 11 H -indolo[3,2-c]quinoline by a two-step protocol involving a regioselective 6- endo -cyclization promoted by the hendrickson reagent

Synthesis

Volumn , Issue 4, 2011, Pages 626-634

  Xu, Min ^a   Hou, Qiwen ^a   Wang, Shaozhong ^a   Wang, Huaqin ^b   Yao, Zhu Jun ^a  

^a NANJING UNIVERSITY   (China)

^b NANJING UNIVERSITY   (China)

Author keywords

alkyne; cyclization; gold; Hendrickson reagent; quinoline

Indexed keywords

ALKYNE; HENDRICKSON REAGENT; QUINOLINE; REGIO-SELECTIVE; TETRACYCLIC SKELETON; TWO-STEP PROTOCOL;

ACETYLENE; GOLD; GOLD COMPOUNDS; REGIOSELECTIVITY;

CYCLIZATION;

11H INDOLO[3,2 C]QUINOLINE; 3 ETHYL 11H INDOLO[3,2 C]QUINOLINE; 6 (4 METHOXYPHENYL) 11H INDOLO[3,2 C]QUINOLINE; 6 (4 NITROPHENYL) 11H INDOLO[3,2 C]QUINOLINE; 6 ETHOXY 11H INDOLO[3,2 C]QUINOLINE; 6 METHYL 11H INDOLO[3,2 C]QUINOLINE; 6 METHYL INDOLO[3,2 C]QUINOLINE; 6 PHENYL 11H INDOLO[3,2 C]QUINOLINE; 6,8 DIMETHYL 11H INDOLO[3,2 C]QUINOLINE; 8 CHLORO 6 METHYL 11H INDOLO[3,2 C]QUINOLINE; 8,9 METHYLENEDIOXY 6 METHYL 11H INDOLO[3,2 C]QUINOLINE; ALKYNE DERIVATIVE; GOLD; INDOLOQUINOLINE DERIVATIVE; NITROGEN; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; CYCLIZATION; DRUG STRUCTURE; INFRARED SPECTROSCOPY; SONOGASHIRA REACTION;

EID: 79651470703     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1258411     Document Type: Article

References (29)

1. For a review, see:, Lavrado J, Moreira R, Paulo A, Curr. Med. Chem. 2010 17 2348
2. Pousset J.-L, Martin M.-T, Jossang A, Bodo B, Phytochemistry 1995 39 735
3. Van Miert S, Hostyn S, Maes B U. W., Cimanga K, Brun R, Kaiser M, Matyus P, Dommisse R, Lemiere G, Vlietinck A, Pieters L, J. Nat. Prod. 2005 68 674
4. Lu C.-M, Chen Y.-L, Chen H.-L, Chen C.-A, Lu P.-J, Yang C.-N, Tzeng C.-C, Bioorg. Med. Chem. 2010 18 1948
5. He L, Chang H.-X, Chou T.-C, Savaraj N, Cheng C.-C, Eur. J. Med. Chem. 2003 38 101
6. Chen Y.-L, Chung C.-H, Chen I.-L, Chen P H., Jeng H.-Y, Bioorg. Med. Chem. 2002 10 2705
7. Dhanabal T, Sangeetha R, Mohan P S., Tetrahedron 2006 62 6258
8. Nandha Kumar R, Suresh T, Mohan P S., Tetrahedron Lett. 2002 43 3327
9. Kraus G A., Guo H, Tetrahedron Lett. 2010 51 4137
10. Beres M, Timari G, Hajos G, Tetrahedron Lett. 2002 43 6035
11. Fresneda P M., Molina P, Delgado S, Tetrahedron 2001 57 6197
12. Fresneda P M., Molina P, Delgado S, Tetrahedron Lett. 1999 40 7275
13. Meyers C, Rombouts G, Loones K T. J., Coelho A, Maes B U. W., Adv. Synth. Catal. 2008 350 465
14. Jonckers T H. M., Maes B U. W., Lemiere G L. F., Rombouts G, Pieters L, Haemers A, Dommisse R A., Synlett 2003 615
15. Agarwal P K., Sawant D, Sharma S, Kundu B, Eur. J. Org. Chem. 2009 292
16. Miki Y, Kuromatsu M, Miyatake H, Hamamoto H, Tetrahedron Lett. 2007 48 9093
17. Cacchi S, Fabrizi G, Pace P, Marinelli F, Synlett 1999 620
18. Sakai N, Annaka K, Konakahara T, J. Org. Chem. 2006 71 3653
19. Sakai N, Annaka K, Fujita A, Sato A, Konakahara T, J. Org. Chem. 2008 73 4160
20. Alfonsi M, Acradi A, Aschi M, Bianchi G, Marinelli F, J. Org. Chem. 2005 70 2265
21. Arcadi A, Bianchi G, Marinelli F, Synthesis 2004 610
22. Hendrickson J B., Schwartzman S M., Tetrahedron Lett. 1975 16 277
23. Wu M, Wang S, Synthesis 2010 587
24. Liu G.-S, Yao Y.-S, Xu P, Wang S, Yao Z.-J, Chem. Asian J. 2010 5 1382
25. Zhou H.-B, Liu G.-S, Yao Z.-J, J. Org. Chem. 2007 72 6270
26. Zhou H.-B, Liu G.-S, Yao Z.-J, Org. Lett. 2007 9 2003
27. You S.-L, Kelly J W., Org. Lett. 2004 6 1681
28. You S.-L, Kelly J W., J. Org. Chem. 2003 68 9506
29. You S.-L, Razavi H, Kelly J W., Angew. Chem. Int. Ed. 2003 42 83