Mild and general one-pot reduction and cyclization of aromatic and heteroaromatic 2-nitroamines to bicyclic 2 H -imidazoles

Synlett

Volumn , Issue 18, 2010, Pages 2759-2764

  Hanan, Emily J ^a   Chan, Bryan K ^a   Estrada, Anthony A ^a   Shore, Daniel G ^a   Lyssikatos, Joseph P ^a  

^a GENENTECH INC   (United States)

Author keywords

cyclization; heterocycles; imidazole; iron; reduction

Indexed keywords

2 NITROAMINE; AMMONIUM CHLORIDE; AROMATIC AMINE; BICYCLIC 2H IMIDAZOLE; FORMIC ACID; IMIDAZOLE DERIVATIVE; IRON; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CYCLIZATION; ONE POT SYNTHESIS; REDUCTION;

EID: 78149280200     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1259007     Document Type: Article

References (47)

1. Horton D A., Bourne G T., Smythe M L., Chem. Rev. 2003 103 893
2. Spasov A A., Yozhitsa I N., Bugaeva L I., Anisimova V A., Pharm. Chem. J. 1999 33 232
3. Ding S, Gray N S., Ding Q, Schultz P G., Tetrahedron Lett. 2001 42 8751
4. Phillips M A., J. Chem. Soc. 1928 2393
5. Wright [nl]J B., Chem. Rev. 1951 48 397
6. Subasinghe N L., Travins J M., Ali F, Huang H, Ballentine S K., Marugan J J., Khalil E, Hufnagel H R., Bone R F., Desjarlais R L., Crysler C S., Ninan N, Cummings [nl]M D., Molloy C J., Tomczuk B E., Bioorg. Med. Chem. Lett. 2006 16 2200
7. Minetti P, Tinti M O., Carminati P, Castorina M, DiCesare M A., Serio S D., Gallo G, Ghirardi O, Giorgi F, Giorgi L, Piersanti G, Bartoccini F, Tarzia G, J. Med. Chem. 2005 48 6887
8. Suzuki N, Tanaka Y, Dohmori R, Chem. Pharm. Bull. 1980 28 235
9. Seley K L., ODaniel P I., Salim S, Nucleosides, Nucleotides Nucleic Acids 2003 22 2133
10. Maron D, Kontorowitsch M, Bloch J.-J, Ber. Dtsch. Chem. Ges. 1914 47 1352
11. vanGalen P J. M., Nissen P, vanWijngaarden I, Ijzerman A P., Soudijn W, J. Med. Chem. 1991 34 1202
12. Palmer B D., Smaill J B., Boyd M, Boschelli D H., Doherty A M., Hamby J M., Khatana S S., Kramer J B., Kraker A J., Panek R L., Lu G H., Dahring T K., Winters R T., Showalter H D. H., Denny W A., J. Med. Chem. 1998 41 5457
13. Boydston A J., Pecinovsky C S., Chao S T., Bielawski C W., J. Am. Chem. Soc. 2007 129 14550
14. Huisgen R, Justus Liebigs Ann. Chem. 1948 559 101
15. Cholody W M., Hernandez L, Hassner L, Scudiero D A., Djurickovic [nl]D B., Michejda C J., J. Med. Chem. 1995 38 3043
16. VanVliet D S., Gillespie P, Scicinski J J., Tetrahedron Lett. 2005 46 6741
17. Chen J J., Thakur K D., Clark M P., Laughlin S K., George K M., Bookland R G., Davis J R., Cabrera E J., Easwaran V, De B, Zhang Y G., Bioorg. Med. Chem. Lett. 2006 16 5633
18. Boydston [nl]A J., Khramov D M., Bielawski C W., Tetrahedron Lett. 2006 47 5123
19. Boydston A J., Vu P D., Dykhno [nl]O L., Chang V, Wyatt A R., Stockett A S., Ritschdorff E T., Shear J B., Bielawski C W., J. Am. Chem. Soc. 2008 130 3143
20. Roth T, Morningstar M L., Boyer P L., Hughes S H., Buckheit R W., Michejda C J., J. Med Chem. 1997 40 4199
21. Nozary H, Piguet C, Tissot P, Bernardinelli G, Bunzli J.-C G., Deschenaux R, Guillon D, J. Am. Chem. Soc. 1998 120 12274
22. Suami T, Day A, J. Org. Chem. 1959 24 1340
23. Piguet C, Bocquet B, Helv. Chim. Acta 1994 77 931
24. McKenzie B M., Miller A K., Wojtecki R J., Johnson J C., Burke K A., Tzeng K A., Mather P T., Rowan S J., Tetrahedron 2008 64 8488
25. Radl S, Hradil P, Coll. Czech. Chem. Commun. 1991 56 2420, Efremov I V., Rogers B N., Duplantier A J., Zhang L, Zhang Q, Maklad N S., US 2008/0312271 A1 2008
26. Wu W.-L, Burnett D A., Spring R, Greenlee W J., Smith M, Favreau L, Fawzi A, Zhang H, Lachowicz [nl]J E., J. Med. Chem. 2005 48 680
27. Foster R, Ing H R., Rogers E F., J. Chem. Soc. 1957 1671
28. (a), Bongartz J.-P, Andre M, Meerpoel L, Boeckx G M., VanLommen G, Buyck C, Obrecht D, Ermert P, Luther A, WO 2008/148840 A1 2008 (b), Popilnichenko S V., Brovarets B S., Drach B S., Russ. J. Org. Chem. 2004 40 219
29. 2 has been reported to reductively cleave isoxazoles:, Auricchio S, Bini A, Pastormerlo E, Truscello A M., Tetrahedron 1997 53 10911
30. Nitro-isoxazoles have been reported to undergo acid-catalyzed thermal isomerization and hydrolysis:, PinhoeMelo T M. V. D., Curr. Org. Chem. 2005 9 925
31. Krasovskiy A, Malakhov V, Gavryushin A, Knochel P, Angew. Chem. Int. Ed. 2006 45 6040
32. Krasovskiy A, Knochel P, Angew. Chem. Int. Ed. 2004 43 3333
33. Wunderlich S H., Knochel P, Angew. Chem. Int. Ed. 2009 48 9717
34. Piller F M., Appukkuttan P, Gavryushin A, Helm M, Knochel P, Angew. Chem. Int. Ed. 2008 47 6802
35. Wundt E, Ber. Dtsch. Chem. Ges. 1878 11 826
36. v.Auwers K, Maws W, Ber. Dtsch. Chem. Ges. 1928 61 2415
37. Fischer O, Rigaud M, Ber. Dtsch. Chem. Ges. 1901 34 4204
38. Sekikawa I, Bull. Chem. Soc. Jpn. 1958 31 252
39. VanVliet D S., Gillespie P, Scicinski J J., Tetrahedron Lett. 2005 46 6741
40. Fischer O, Ber. Dtsch. Chem. Ges. 1904 37 557
41. Rabiger D J., Joullie M M., J. Chem. Soc. 1964 915
42. Rabiger D J., Joullie M M., J. Org. Chem. 1961 26 1649
43. Howell J R., Rasmussen M, Austr. J. Chem. 1993 46 1177
44. Robinson F M., Miller I M., McPherson J F., Folkers K, J. Am. Chem. Soc. 1955 77 5192
45. Weidenhagen R, Weeden U, Ber. Dtsch. Chem. Ges. 1938 71 2347
46. Graboyes H, Day A R., J. Am. Chem. Soc. 1957 79 6421
47. Rousseau R J., Robins R K., J. Heterocycl. Chem. 1965 2 196