Iron Sulfide Catalyzed Redox/Condensation Cascade Reaction between 2-Amino/Hydroxy Nitrobenzenes and Activated Methyl Groups: A Straightforward Atom Economical Approach to 2-Hetaryl-benzimidazoles and -benzoxazoles

Journal of the American Chemical Society - Tập 135 Số 1 - Trang 118-121 - 2013
Thanh Bình Nguyễn1, Ludmila Ermolenko1
1Centre de Recherche de Gif-sur-Yvette, Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex, France

Tóm tắt

Từ khóa


Tài liệu tham khảo

Johnson M. K., 2005, Iron–sulfur proteins in: Encyclopedia of Inorganic Chemistry, 2

Spiro T. G., 1982, Iron-Sulfur Proteins

Amstrong F., 1982, Adv. Inorg. Bioinorg. Mech., 1, 65

cStiefel, E. I.; George, G. N.Ferredoxins, Hydrogenases, and Nitrogenases: Metal-Sulfide Proteins in Bioinorganic Chemistry;University Science Books: 1994; pp365–455.

Herskovitz T., 1972, Proc. Natl. Acad. Sci. U.S.A., 69, 2437, 10.1073/pnas.69.9.2437

Johnson D., 2005, Annu. Rev. Biochem., 74, 247, 10.1146/annurev.biochem.74.082803.133518

Berg, J. M.; Holm, R. H.Iron-Sulfur Proteins;Spiro, T. G., Ed.John Wiley and Sons: 1981; pp1–66.

Maden B. E. H., 1995, Trends Biochem. Sci., 20, 337, 10.1016/S0968-0004(00)89069-6

Abou-Jneid R., 2004, Org. Lett., 6, 3933, 10.1021/ol048529e

Schroif-Gregoire C., 2006, Org. Lett., 8, 2961, 10.1021/ol0608451

Vergne C., 2008, Org. Lett., 10, 493, 10.1021/ol702866m

Nguyen T. B., 2008, Org. Lett., 10, 4493, 10.1021/ol8017243

Picon S., 2009, Org. Lett., 11, 2523, 10.1021/ol900745c

Nguyen T. B., 2010, J. Org. Chem., 75, 611, 10.1021/jo902107j

Nguyen T. B., 2012, Org. Lett., 14, 3202, 10.1021/ol301308c

Nguyen T. B., 2012, Org. Lett., 14, 4274, 10.1021/ol3020368

10.3987/COM-12-S(N)53

Nguyen T. B., 2012, Org. Lett., 14, 5948, 10.1021/ol302856w

Charton J., 2005, Chem. Pharm. Bull., 53, 492, 10.1248/cpb.53.492

Seijas J. A., 2007, Synlett, 313, 10.1055/s-2007-967994

Maradolla M. B., 2008, ARKIVOC, 15, 42, 10.3998/ark.5550190.0009.f05

Sharghi H., 2009, Synth. Commun., 39, 860, 10.1080/00397910802431214

Wen X., 2012, Tetrahedron Lett., 53, 2440, 10.1016/j.tetlet.2012.03.007

Harrop T. C., 2003, Synth. Commun., 33, 1943, 10.1081/SCC-120020209

Brembilla A., 1990, Synth. Commun., 20, 3379, 10.1080/00397919008051575

Khilya V., 1970, Chem. Heterocycl. Compd., 6, 1584, 10.1007/BF00522589

Quast H., 1993, Chem. Ber., 126, 503, 10.1002/cber.19931260230

Hofmann A. W., 1880, Chem. Ber., 13, 1238, 10.1002/cber.188001301333

Shi D. F., 1996, J. Med. Chem., 39, 3375, 10.1021/jm9600959

Kourounakis A., 2008, J. Med. Chem., 51, 5861, 10.1021/jm800663w

Campagne E., 1958, J. Org. Chem., 23, 1344, 10.1021/jo01103a029

Chakraborti A. K., 2004, Synlett, 1533, 10.1055/s-2004-829089

Bastug G., 2012, Org. Lett., 14, 3502, 10.1021/ol301472a

Patil A. V., 2010, Bull. Korean Chem. Soc., 31, 1719, 10.5012/bkcs.2010.31.6.1719

Mohammadpoor-Baltork I., 2007, Monatsh. Chem., 138, 663, 10.1007/s00706-007-0655-9

Mohammadpoor-Baltork I., 2007, Catal. Commun., 8, 1865, 10.1016/j.catcom.2007.02.020

Sheng C., 2011, Eur. J. Med. Chem., 46, 1706, 10.1016/j.ejmech.2011.01.075

Kristinsson H., 1979, Synthesis, 102, 10.1055/s-1979-28571

Gomez E., 1986, Tetrahedron, 42, 2625, 10.1016/S0040-4020(01)90547-2

Katritzky A. R., 1988, Synth. Commun., 18, 651, 10.1080/00397918808077350

Harb A. F. A., 1986, Heterocycles, 24, 1873, 10.3987/R-1986-07-1873

Kornilov M. Y., 1973, Zhur. Org. Khim., 9, 2188

yBotta, A.U.S. Patent US3972890 A1, 1976.

Wu M., 2012, Org. Lett., 14, 2722, 10.1021/ol300937z

aWuppwetal-Elberfeld, H. A. O.DE949059, 1953.

Yutilov Y. M., 1994, Russian J. Org. Chem., 30, 461

Rickard D., 2007, Chem. Rev., 107, 514, 10.1021/cr0503658

Venkateswara Rao P., 2004, Chem. Rev., 104, 527, 10.1021/cr020615+

Gres’ko S. V., 2001, Russian J. Org. Chem., 37, 1026, 10.1023/A:1012490919797

bAhlmark, M.; Bäckström, R.; Luiro, A.; Pystynen, J.; Tiainen, E.WO2007/10085 A2, 2007.

Yutilov Y. M., 1989, Chem. Heterocycl. Compd., 25, 783, 10.1007/BF00472751

Mazzone G., 1984, J. Heterocycl. Chem., 21, 181, 10.1002/jhet.5570210136

Hisano T., 1982, Chem. Pharm. Bull., 30, 2996, 10.1248/cpb.30.2996

Emmert B., 1954, Chem. Ber., 87, 676, 10.1002/cber.19540870509

Saikachi H., 1959, Chem. Pharm. Bull., 7, 716, 10.1248/cpb.7.716

Porter H. D., 1954, J. Am. Chem. Soc., 76, 127, 10.1021/ja01630a035

Miller P. E., 1957, J. Org. Chem., 22, 664, 10.1021/jo01357a020

jWürzburg, B. E.; Wuppwetal-Elberfeld, H. A. O.; Köln-Mülheim, M. G.; Würzburg, A. H.DE930926, 1953.Sulfur has been shown to act as a reducing agent in basic media for an aromatic nitro group:

McLaughlin M. A., 2006, Tetrahedron Lett., 47, 9095, 10.1016/j.tetlet.2006.10.079

Niknam K., 2003, Phosphorus, Sulfur Silicon Relat. Elem., 178, 1385, 10.1080/10426500307905

Kas’yan O. A., 2002, Russian J. Org. Chem., 38, 165, 10.1023/A:1015545128873

Huber D., 1988, Tetrahedron Lett., 29, 635, 10.1016/S0040-4039(00)80169-0

Sato R., 1979, Phosphorus, Sulfur Relat. Elem., 7, 229, 10.1080/03086647908077473

Porter H. K., 1973, Org. React., 20, 455

Cope O. J., 1962, Can. J. Chem., 40, 2317, 10.1139/v62-355

Hirao N., 1950, J. Osaka Inst. Sci. Technol., 1, 57

Hamana H., 1983, Chem. Lett., 333, 10.1246/cl.1983.333

Hamana H., 1984, Chem. Lett., 1591, 10.1246/cl.1984.1591

Pryor W. A., 1962, Mechanism of Sulfur Reactions

Perregaard J., 1975, Acta Chem. Scand. B, 29, 538, 10.3891/acta.chem.scand.29b-0538