Three-component synthesis of cryofluorescent 2,4-disubstituted 3H-1,5-benzodiazepines - Conformational control of emission properties

European Journal of Organic Chemistry

Volumn , Issue 28, 2008, Pages 4796-4805

  Willy, Benjamin ^a   Dallos, Timea ^b   Rominger, Frank ^c   Schönhaber, Jan ^a   Müller, Thomas J J ^a  

^a HEINRICH HEINE UNIVERSITY   (Germany)

^b BABE BOLYAI UNIVERSITY   (Romania)

^c UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

Benzodiazepines; C C coupling; Cyclocondensation; Fluorescence; Microwave assisted reactions; Multicomponent reactions

Indexed keywords

EID: 52249104499     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200800619     Document Type: Article

References (64)

1. For reviews, see, for example a) G. A. Archer, L. H. Sternbach, Chem. Rev. 1968, 68, 747-784;
2. b) F. D. Popp, A. C. Noble, Adv. Heterocycl. Chem. 1967, 8, 21-82;
3. c) L. H. Sternbach, Angew. Chem. 1971, 83, 70-79;
4. Angew. Chem. Int. Ed. Engl. 1971, 10, 34-43;
5. d) J. L. Vanderheyden, J. E. Vanderheyden, J. Pharm. Belg. 1981, 36, 354-364;
6. e) G. R. Jones, P. P. Singer, Adv. Anal. Toxicol. 1989, 2, 1-69;
7. f) J. B. Bremner in Comprehensive Heterocyclic Chemistry II (Eds.: A. R. Katritzky, C. W. Rees, E. F. V. Scriven), Pergamon Press, Oxford, New York, Toronto, Sydney, Paris, Frankfurt, 1996, Vol. 9, 183-189.
8. For synthetic and pharmacological studies, see, for example a) A. Zellou, Y. Cherrah, M. Hassar, E.-M. Essassi, Ann. Pharm. Fr. 1998, 56, 169-174;
9. b) F. Savelli, A. Boido, A. Mule, L. Piu, M. C. Alamanni, G. Pirisino, M. Satta, A. Peana, Farmaco 1989, 44, 125-140;
10. c) A. Nawojski, W. Nawrocka, H. Liszkiewicz, Pol. J. Pharmacol. Pharm. 1985, 37, 69-72;
11. d) M. Wilimowski, K. Orzechowsa-Juzwenko, J. Barczynska, L. Kedzierska-Gozdzik, M. Witkowska, W. Wojewodzki, E. Dus, T. Plawiak, J. Gryska, H. Maska, Pol. J. Pharmacol. Pharm. 1983, 35, 89-102;
12. e) V. K. Srivastava, R. K. Satsangi, K. Kishore, Arzneim.-Forsch. 1982, 32, 1512-1514.
13. a) H. Schutz, Benzodiazepines, Springer, Heidelberg, 1982;
14. b) J. K. Landquist, in Comprehensive Heterocyclic Chemistry (Eds.: A. R. Katritzky, C. W. Rees), Pergamon, Oxford, 1984, vol. 1, pp. 166-170;
15. c) R. I. Fryer, Bicyclic Diazepines, in Comprehensive Heterocyclic Chemistry (Ed.: E. C. Taylor), Wiley, New York, 1991, vol. 50, chapter II;
16. d) L. O. Randall, B. Kappel, in Benzodiazepines (Eds.: S. Garattini, E. Musini, L. O. Randall), Raven Press, New York, 1973, p. 27.
17. J. R. De Baun, F. M. Pallos, D. R. Baker, U. S. Patent, US 3978227 19760831, 1976.
18. For synthetic and pharmacological studies, see, for example a) K. A. Parker, A. Dermatakis, J. Org. Chem. 1997, 62, 4164-4167;
19. b) K. D. Hargrave, G. Schmidt, W. Engel, V. Austel, Patent Application: US 91-650141 19910204. Patent Priority: US 89-340937 19890420; US 89-372728 19890628; US 89-438922 19891117; US 90-600554 19901019.
20. R. C. Harris, J. M. Straley, French Patent, FR 1537757 19680830, 1968.
21. a) M. C. Aversa, A. Ferlazzo, P. Gionnetto, F. H. Kohnke, Synthesis 1986, 230-231;
22. b) M. Essaber, A. Hasnaoui, A. Benharref, J. P. Lavergne, Synth. Commun. 1998, 28, 4097-4104;
23. c) A. M. ElSayed, H. Abdel-Ghany, A. M. M. El-Saghier, Synth. Commun. 1999, 29, 3561-3572;
24. d) A. Chimirri, S. Grasso, R. Ottana, G. Romeo, M. Zappala, J. Heterocycl. Chem. 1990, 27, 371-374.
25. W. Ried, E. Torinus, Chem. Ber. 1959, 92, 2902-2916.
26. a) P. Stahlhofen, W. Ried, Chem. Ber. 1957, 90, 815-824;
27. b) G. K. Nagaraja, V. P. Vaidya, K. S. Rai, K. M. Mahadevan, Phosphorus Sulfur Silicon Relat. Elem. 2006, 181, 2797-2806;
28. [14b,14c]), a related synthesis was recently published; see c) S. S. Palimkar, R. J. Lahoti, K. V. Srinivasan, Green Chem. 2007, 9, 146-152;
29. d) T. J. J. Müller, A. S. Karpov, Ger. Offen. 2005, DE 10328400 A1 20050113.
30. a) J. S. Yadav, B. V. S. Reddy, S. Praveenkumar, K. Nagaiah, Synthesis 2005, 480-484;
31. b) G. Sabitha, G. S. K. Reddy, K. B. Reddy, N. M. Reddy, J. S. Yadav, Adv. Synth. Catal. 2004, 346, 921-923;
32. c) M. Curini, F. Epifano, M. C. Marcotullio, O. Rosati, Tetrahedron Lett. 2001, 42, 3195-3197;
33. d) J. S. Yadav, B. V. S. Reddy, B. Eshwaraiah, K. Anuradha, Green Chem. 2002, 4, 592-594;
34. e) B. Kaboudin, K. Naveen, Heterocycles 2001, 55, 1443-1446;
35. f) M. Pozaretzi, J. S. Stephanatou, C. A. Tsoleridis, Tetrahedron Lett. 2002, 43, 1755-1758.
36. D. V. Jarikote, S. A. Siddiqui, R. Rajagapol, T. Daniel, R. J. Lahoti, K. V. Srinivasan, Tetrahedron Lett. 2003, 44, 1835-1838.
37. M. S. Balakrishna, B. Kaboudin, Tetrahedron Lett. 2001, 42, 1127-1129.
38. a) T. J. J. Müller, D. M. D'Souza, Pure Appl. Chem. 2008, 80, 609-620;
39. b) T. J. J. Müller in Functional Organic Materials - Synthesis Strategies, and Applications (Eds.: T. J. J. Müller, U. H. F. Bunz), Wiley-VCH, Weinheim, 2007, pp. 179-223.
40. For a recent review on multicomponent synthesis of heterocycles by transition metal catalysis, see: a) D. M. D'Souza, T. J. J. Müller, Chem. Soc. Rev. 2007, 36, 1095-1108;
41. b) T. J. J. Müller, Chim. Oggi/Chem. Today 2007, 25, 70-78;
42. c) T. J. J. Müller, Targets Heterocycl. Systems 2006, 10, 54-65.
43. For lead reviews on Sonogashira couplings, see for example a) S. Takahashi, Y. Kuroyama, K. Sonogashira, N. Hagihara, Synthesis 1980, 627-630;
44. b) K. Sonogashira in Metal catalyzed Cross-coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, pp. 203-229;
45. c) K. Sonogashira, J. Organomet. Chem. 2002, 653, 46-49;
46. d) E.-I. Negishi, L. Anastasia, Chem. Rev. 2003, 103, 1979-2018;
47. e) J. A. Marsden, M. M. Haley in Metal catalyzed Cross-coupling Reactions (Eds.: A. de Meijere, F. Diederich), Wiley-VCH, Weinheim, 2004, 319-345;
48. f) H. Doucet, J.-C. Hierso, Angew. Chem. Int. Ed. 2007, 46, 834-871;
49. g) L. Yin, J. Liebscher, Chem. Rev. 2007, 107, 133-173.
50. Y. Toda, K. Sonogashira, N. Hagihara, Synthesis 1977, 777-778.
51. a) A. S. Karpov, T. J. J. Müller, Org. Lett. 2003, 5, 3451-3454;
52. b) A. S. Karpov, T. J. J. Müller, Synthesis 2003, 2815-2826;
53. c) A. S. Karpov, E. Merkul, F. Rominger, T. J. J. Müller, Angew. Chem. 2005, 117, 7112-7117;
54. Angew. Chem. Int. Ed. 2005, 44, 6951-6956;
55. d) A. S. Karpov, E. Merkul, F. Rominger, T. J. J. Müller, Eur. J. Org. Chem. 2006, 2991-3000;
56. e) E. Merkul, T. J. J. Müller, Chem. Commun. 2006, 4817-4819;
57. f) B. Willy, F. Rominger, T. J. J. Müller, Synthesis 2008, 293-303.
58. B. Willy, T. J. J. Müller, Eur. J. Org. Chem. 2008, 4157-4168.
59. a) A. Mannschreck, G. Rissmann, F. Vögtle, D. Wild, Chem. Ber. 1967, 100, 335-346;
60. b) R. Ahmad, M. Zia-ul-Haq, H. Duddeck, L. Stefaniak, J. Sitkowski, Monatsh. Chem. 1997, 128, 633-640.
61. CCDC-692628 (of 6f) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via http://www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Center, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: +44-1223-336-033; or deposit@ccdc.cam.ac.uk).
62. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian 03, Revision B.03 ed., Gaussian Inc., Wallingford CT, 2004.
63. D. Lloyd, H. McNab, Adv. Heterocycl. Chem. 1998, 71, 1-56.
64. G. Cabarrocas, S. Rafel, M. Ventura, J. M. Villalgordo, Synlett 2000, 595-598.