Novel synthesis of 2-aminobenzimidazoles from isoselenocyanates

Synlett

Volumn , Issue 6, 2010, Pages 901-904

  Xie, Yuanyuan ^a   Zhang, Fan ^a   Li, Jianjun ^a   Shi, Xiangjun ^a  

^a ZHEJIANG UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

2 aminobenzimidazoles; Cyclization; Isoselenocyanates; Selenium recycling

Indexed keywords

BENZIMIDAZOLE DERIVATIVE; CYANIC ACID DERIVATIVE; SELENIUM DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DRUG SYNTHESIS; ONE POT SYNTHESIS;

EID: 77949900891     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1219395     Document Type: Article

References (23)

1. Janssens F, Torremans J, Janssen M, Stokbroekx [nl]R A., Luyckx M, Janssen P A., J. Med. Chem. 1985 28 1925
2. Bovet D, Bovet-Nitti F, Médicaments du Système Nerveux Végétatif 5th ed. Karger Basel 1948 741
3. The Extra Pharmacopeia 27th ed., Wade A, The Pharmaceutical Press London 1978 1287
4. Martin E J., Critchlow R E., J. Comb. Chem. 1999 1 32
5. Beaulieu C, Wang Z, Denis D, Greig G, Lamontagne S, ONeill G, Slipetz D, Wang J, Bioorg. Med. Chem. Lett. 2004 14 3195
6. Kling A, Backfisch G, Delzer J, Geneste H, Graef C, Hornberger W, Lange U E. W., Lauterbach A, Seitz W, Subkowski T, Bioorg. Med. Chem. 2003 11 1319
7. Snow R J., Cardozo M G., Morwick T M., Busacca C A., Dong Y, Eckner R J., Jacober S, Jakes S, Kapadia S, Lukas S, Panzenbeck M, Peet G W., Peterson J D., Prokopowicz A S. III., Sellati R, Tolbert R M., Tschantz M A., Moss N, J. Med. Chem. 2002 45 3394
8. Carpenter R D., DeBerdt P B., Lam K S., Kurth M J., [nl]J. Comb. Chem. 2006 8 907
9. Perkins J J., Zartman A E., Meissner R S., Tetrahedron Lett. 1999 40 1103
10. Omar A.-M M. E., Ragab M S., Farghaly A M., Barghash A M., Pharmazie 1976 31 348
11. Wang X.-J, Zhang L, Xu Y, Krishnamurthy D, Senanayake C H., Tetrahedron Lett. 2004 45 7167
12. Omar A.-M M. E., Synthesis 1974 41
13. Heinelt U, Schultheis D, Jager S, Lindenmaier M, Pollex A, Beckmann H S. G., Tetrahedron 2004 60 9883
14. Omar A.-M M. E., Habib N S., Aboulwafa [nl]O M., Synthesis 1977 864
15. Cee V J., Downing N S., Tetrahedron Lett. 2006 47 3747
16. Heimgartner H, Zhou Y, Atanassov P K., Sommen G L., Phosphorus, Sulfur Silicon Relat. Elem. 2008 183 840
17. Fernández-Bola?os J G., L?pez O, Ulgar V, Maya I, Fuentes J, Tetrahedron Lett. 2004 45 4081
18. Koketsu M, Sakai T, Kiyokuni T, Garud D R., Ando H, Ishikara H, Heterocycles 2006 68 1607
19. Dobson D C., James F C., Safarik I, Gunning H E., Strausz O P., J. Phys. Chem. 1975 75 771
20. Pittman R W., J. Chem. Soc. 1949 1811
21. Typical Procedure for Compound 2e A mixture of 1-isoselenocyanato-4- methoxybenzene (1e;0.212 g, 1 mmol) and phenylene-1,2-diamine (0.108 g, 1 mmol) were suspended in CHCl3 (20 mL). The reaction was carried out at r.t. After 10 min the reaction was ceased, and the reaction mixture was concentrated under vacuum. The residue was washed with a mixture of hexane and EtOAc (hexane?EtOAc = 20:1) to obtain 1-(2-aminophenyl)-3-(4-methoxyphenyl) selenourea (2e) as a yellow solid (0.313 g, 98% yield). 1H NMR (400 MHz, DMSO-d6): d = 9.63 (s, 1 H), 9.34 (s, 1 H), 7.26?7.29 (m, 2 H), 6.96?7.02 (m, 2 H), 6.87?6.90 (m, 2 H), 6.74 (dd, 1 H, J = 1.2, 8.0 Hz), 6.56 (dt,1 H, J = 1.6, 7.6 Hz), 4.89 (s, 2 H), 3.74 (s, 3 H). 13C NMR (100 MHz, DMSO-d6): d = 178.8, 157.0, 143.9, 132.5, 128.2, 127.4, 127.0, 124.4, 116.4, 115.9, 113.5, 55.2. HRMS (EI): m/z calcd for C14H15N3OSe: 320.0302; found:320.0317.
22. Procedure for Controlled Experiment 1-(2-aminophenyl)-3-(4-methoxyphenyl) selenourea (2e, 1 mmol) was suspended in DMF (20 mL) with magnetic stirring. The reaction was carried out at 70 ?C. A lightavoiding control and a nitrogen-atmosphere control reaction were set up at the same time. The reaction was monitored by TLC. 2-Aminophenylselenourea was totally converted into 3e after 4 h in normal and light-avoiding control. The reaction in nitrogen atmosphere was prolonged to 36 h, but only trace of 3e was found.
23. +