Carbene-mediated transformations of 1-(benzylideneamino)benzimidazoles

Journal of Organic Chemistry

Volumn 76, Issue 10, 2011, Pages 4082-4087

  Katritzky, Alan R ^a   Jishkariani, Davit ^a   Sakhuja, Rajeev ^a   Hall, C Dennis ^a   Steel, Peter J ^b  

^a University of Florida   (United States)

^b UNIVERSITY OF CANTERBURY   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

BENZIMIDAZOLES; ISOTHIOCYANATES; ROOM TEMPERATURE;

CARBON DISULFIDE;

ORGANIC COMPOUNDS;

(1,3 DIMETHYLBENZIMIDAZOL 3 IUM 2 CARBOTHIOYL)ISOPROPYLAZANIDE; 1 (BENZYLIDENEAMINO)BENZIMIDAZOLE DERIVATIVE; 1 [(4 BROMO 2 THIENYL)METHYLENEAMINO] 3 BUTYLBENZIMIDAZOL 3 IUM 2 CARBODITHIOATE; 1 [BENZYLIDENEAMINO] 3 BUTYLBENZIMIDAZOL 3 IUM 2 CARBODITHIOATE; 1 BUTYL 1',3' DIISOPROPYL 3 [(4 METHOXYPHENYL)METHYLENEAMINO]SPIRO[BENZIMIDAZOL 2,5' IMIDAZOLIDINE] 2',4' DITHIONE; 1 BUTYL 3 [(4 METHOXYPHENYL)METHYLENEAMINO]BENZIMIDAZOL 1 IUM 2 CARBODITHIOATE; 1,3 DIMETHYLBENZIMIDAZOL 3 IUM 2 CARBODITHIOATE; 1[BENZYLIDENEAMINO] 3 BUTYL 1',3' DIISOPROPYLSPIRO[BENZIMIDAZOL 2,5' IMIDAZOLIDINE] 2',4' DITHIONE; 3 [(4 METHOXYPHENYL)METHYLENEAMINO]BENZIMIDAZOL 1 IUM 1 AMINE 2,4 DINITROPHENOLATE; 3 [4 TOLYLMETHYLENEAMINO]BENZIMIDAZOL 1 IUM 1 AMINE 2,4 DINITROPHENOLATE; 3 [[4 (DIETHYLAMINO)PHENYL]METHYLENEAMINO]BENZIMIDAZOL 1 IUM 1 AMINE 2,4 DINITROPHENOLATE; BENZIMIDAZOL 3 IUM 1,3 DIAMINE 2,4 DINITROPHENOLATE; BENZIMIDAZOLE DERIVATIVE; BENZOYL (1,3 DIMETHYLBENZIMIDAZOL 3 IUM 2 CARBOTHIOYL)AZANIDE; BENZOYL [1 (4 BROMO 2 THIENYL)METHYLENEAMINO] 3 BUTYLBENZIMIDAZOL 3 IUM 2 CARBOTHIOYL]AZANIDE; BENZOYL [1 [BENZYLIDENEAMINO] 3 BUTYLBENZIMIDAZOL 3 IUM 2 CARBOTHIOYL]AZANIDE; BENZOYL [1 BUTYL 3[(4 METHOXYPHENYL)METHYLENEAMINO]BENZIMIDAZOL 1 IUM 2 CARBOTHIOYL]AZANIDE; CARBENE; CARBON DISULFIDE; ISOTHIOCYANIC ACID DERIVATIVE; NITROGEN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; PROTON TRANSPORT; ROOM TEMPERATURE; X RAY DIFFRACTION;

BENZIMIDAZOLES; CATALYSIS; METHANE; MODELS, MOLECULAR; MOLECULAR CONFORMATION;

EID: 79956104083     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo200088s     Document Type: Article

References (50)

1. Shimakawa, Y.; Morikawa, T.; Sakaguchi, S. Tetrahedron Lett. 2010, 51, 1786-1789
2. Enders, D.; Balensiefer, T. Acc. Chem. Res. 2004, 37, 534-541
3. Liu, Q.; Rovis, T. J. Am. Chem. Soc. 2006, 128, 2552-2553
4. DiRocco, D. A.; Oberg, K. M.; Dalton, D. M.; Rovis, T. J. Am. Chem. Soc. 2009, 131, 10872-10874
5. Zhang, Y.-R.; He, L.; Wu, X.; Shao, P.-L.; Ye, S. Org. Lett. 2008, 10, 277-280
6. De Sarkar, S.; Studer, A. Org. Lett. 2010, 12, 1992-1995
7. Yang, L.; Tan, B.; Wang, F.; Zhong, G. J. Org. Chem. 2009, 74, 1744-1746
8. Connor, E. F.; Nyce, G. W.; Myers, M.; Möck, A.; Hedrick, J. L. J. Am. Chem. Soc. 2002, 124, 914-915
9. Nyce, G. W.; Glauser, T.; Connor, E. F.; Möck, A.; Waymouth, R. M.; Hedrick, J. L. J. Am. Chem. Soc. 2003, 125, 3046-3056
10. Csihony, S.; Nyce, G. W.; Sentman, A. C.; Waymouth, R. M.; Hedrick, J. L. Polym. Prepr. 2004, 45, 319-320
11. Grasa, G. A.; Kissling, R. M.; Nolan, S. P. Org. Lett. 2002, 4, 3583-3586
12. Marion, N.; Diez-González, S.; Nolan, S. P. Angew. Chem., Int. Ed. 2007, 46, 2988-3000
13. Wanzlick, H. W. Angew. Chem. 1962, 74, 129-134
14. Choi, T.-L.; Grubbs, R. H. Chem. Commun. 2001, 2648-2649
15. Uchida, T.; Katsuki, T. Tetrahedron Lett. 2009, 50, 4741-4743
16. Arduengo, A. J., III; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1991, 113, 361-363
17. Nair, V.; Bindu, S.; Sreekumar, V. Angew. Chem., Int. Ed. 2004, 43, 5130-5135
18. Wanzlick, H. W.; Schikora, E. Angew. Chem. 1960, 72, 494
19. Wanzlick, H. W.; Schoenherr, H. J. Angew. Chem., Int. Ed. Engl. 1968, 7, 141-142
20. Cheng, Y.; Meth-Cohn, O. Chem. Rev. 2004, 104, 2507-2530
21. Nair, V.; Rajesh, C.; Vinod, A. U.; Bindu, S.; Sreekanth, A. R.; Mathen, J. S.; Balagopal, L. Acc. Chem. Res. 2003, 36, 899-907
22. Ma, C.; Ding, H.; Zhang, Y.; Bian, M. Angew. Chem., Int. Ed. 2006, 45, 7793-7797
23. Nair, V.; Sreekumar, V.; Bindu, S.; Suresh, E. Org. Lett. 2005, 7, 2297-2300
24. Zhou, H.; Zhang, W.-Z.; Liu, C.-H.; Qu, J.-P.; Lu, X.-B. J. Org. Chem. 2008, 73, 8039-8044
25. Schoessler, W.; Regitz, M. Chem. Ber. 1974, 107, 1931-1948
26. Duong, H. A.; Tekavec, T. N.; Arif, A. M.; Louie, J. Chem. Commun. 2004, 112-113
27. Winberg, H. E.; Coffman, D. D. J. Am. Chem. Soc. 1965, 87, 2776-2777
28. Delaude, L.; Demonceau, A.; Wouters, J. Eur. J. Inorg. Chem. 2009, 1882-1891
29. Küçükbay, H.; Durmaz, R.; Orhan, E.; Günal, S. Farmaco 2003, 58, 431-437
30. Pesch, J.; Harms, K.; Bach, T. Eur. J. Org. Chem. 2004, 2025-2035
31. Coulembier, O.; Dove, A. P.; Pratt, R. C.; Sentman, A. C.; Culkin, D. A.; Mespouille, L.; Dubois, P.; Waymouth, R. M.; Hedrick, J. L. Angew. Chem., Int. Ed. 2005, 44, 4964-4968
32. Hardman, N. J.; Abrams, M. B.; Pribisko, M. A.; Gilbert, T. M.; Martin, R. L.; Kubas, G. J.; Baker, R. T. Angew. Chem., Int. Ed. 2004, 43, 1955-1958
33. Blanrue, A.; Wilhelm, R. Synthesis 2009, 583-586
34. Blanrue, A.; Wilhelm, R. Synlett 2004, 2621-2623
35. Krasuski, W.; Nikolaus, D.; Regitz, M. Liebigs Ann. Chem. 1982, 1451-1465
36. Naeem, S.; Delaude, L.; White, A. J. P.; Wilton-Ely, J. D. E. T. Inorg. Chem. 2010, 49, 1784-1793
37. Kucukbay, H.; Cetinkaya, E.; Durmaz, R. Arzneim. Forsch. 1995, 45, 1331-1334
38. Li, J.-Q.; Liao, R.-Z.; Ding, W.-J.; Cheng, Y. J. Org. Chem. 2007, 72, 6266-6269
39. Cheng, Y.; Wang, B.; Wang, X.-R.; Zhang, J.-H.; Fang, D.-C. J. Org. Chem. 2009, 74, 2357-2367
40. Balch, A. L.; Parks, J. E. J. Am. Chem. Soc. 1974, 96, 4114-4121
41. Alcarazo, M. R.; Roseblade, S. J.; Alonso, E.; Fernández, R.; Alvarez, E.; Lahoz, F. J.; Lassaletta, J. M. J. Am. Chem. Soc. 2004, 126, 13242-13243
42. Ros, A.; Monge, D.; Alcarazo, M.; Álvarez, E.; Lassaletta, J. M.; Fernández, R. Organometallics 2006, 25, 6039-6046
43. Pozharskii, A. F.; Kuz′menko, V. V.; Bumber, A. A.; Petrov, E. S.; Terekhova, M. I.; Chikina, N. L.; Nanavyan, I. M. Khim. Geterotsikl. Soedin. 1989, 221-227
44. Katritzky, A. R.; Laurenzo, K. S. J. Org. Chem. 1988, 53, 3978-3982
45. Sheng, M. N.; Day, A. R. J. Org. Chem. 1963, 28, 736-740
46. Kuznetsov, L. I.; Kolodyazhnyi, Y. V.; Vlotskaya, O. A.; Chikina, N. L.; Kuz′menko, V. V.; Garnovskii, A. D. Koord. Khim. 1982, 8, 445-453
47. Kinoshita, A.; Takei, Y.; Goto, S. Jpn. Kokai Tokkyo Koho 1988, JP63184760, CAN, 110:31371
48. Bostai, B.; Novák, Z.; Bényei, A. C.; Kotschy, A. Org. Lett. 2007, 9, 3437-3439
49. Pozharskii, A. F.; Kuz′menko, V. V.; Foces-Foces, C.; Llamas-Saiz, A. L.; Claramunt, R. M.; Sanz, D.; Elguero, J. J. Chem. Soc., Perkin Trans. 2 1994, 841-846
50. Legault, C.; Charette, A. B. J. Org. Chem. 2003, 68, 7119-7122