Synthesis, Table of Contents PAPER © Georg Thieme Verlag Stuttgart · New York Synthesis of 3-EWG-Substituted 2-Amino-5-hydroxyindoles via Nenitzescu Reaction Jens Landwehr, Reinhard Troschütz*Institut für Pharmazie und Lebensmittelchemie im Emil-Fischer-Centrum, Friedrich-Alexander-Universität, Schuhstr. 19, 91052 Erlangen, Germany Fax: +49(9131)8522587; e-Mail: Troschuetz@pharmazie.uni-erlangen.de; Recommend Article Abstract Buy Article All articles of this category Abstract A series of primary ketene aminals 2, substituted with an electron-withdrawing group were reacted with 1,4-benzoquinone (1) yielding new 3-EWG-substituted 2-amino-5-hydroxyindoles 3a-f. Treatment of ethyl 3,3-diaminoacrylate (2a) with naphthoquinone (20a) and heteroaromatic quinones 20b-d afforded [g]annulated 2-aminoindole-3-carboxylates 21a-d. Key words indoles - quinones - Michael reaction - nucleophilic addition - Nenitzescu reaction Full Text References References 1 Bundy GL. Ayer DE. Banitt LS. Belonga KL. Mizsak SA. Palmer JR. Tustin JM. Chin JE. Hall ED. Linsemann KL. Richards IM. Scherch HM. Sun FF. Yoners PA. Larson PG. Lin JM. Padbury GE. Aaron CS. Mayo JK. J. Med. Chem. 1995, 38: 4161 2a Traxler PM. Furet P. Mett H. Buchdunger E. Meyer T. Lyndon N. J. Med. Chem. 1996, 39: 2285 2b Lowinger T, Shimazaki M, Sato H, Tanaka K, Tsuno N, Marx K, Yamamoto M, Urbahns K, Gantner F, Okigami H, Nakashima K, Takeshita K, Bacon K, Komura H, and Yoshida N. inventors; PCT Int. Appl. WO 2003037898. ; Chem. Abstr. 2003, 138, 368906 3 Bundy G. Banitt LS. Doborowski PJ. Palmer JR. Schwartz TM. Zimmermann DC. Lipton MF. Mauragis MA. Veley MF. Appell RB. Clouse RC. Daugs ED. Org. Process Res. Dev. 2001, 5: 144 4 Dotzauer B. Troschütz R. Synlett 2004, 1039 5a Allen GR. Org. React. 1973, 20: 33 5b Kuckländer U. Tetrahedron 1973, 29: 924 5c Granik VG. Lyubchanskaya VM. Mukhanova TI. Khim. Farm. Zh. 1993, 27: 37 ; Pharm. Chem. J. 1993, 413 6a Grob CA. Weissbach O. Helv. Chim. Acta 1961, 44: 1748 6b Showalter HD. Bridges AJ. Zhou H. Sercel AD. McMichael A. Fry DW. J. Med. Chem. 1999, 42: 5464 6c Glushkov RG. Volskova VA. Magidson OYu. Khim. Farm. Zh. 1976, 1: 25 7 Arnould JC, Bird TG, Boyle FT, and Blackey DC. inventors; PTC Int. Appl. WO 2001092224. 8a Player MR. Li-Chang W. Bayomi SM. Sowell JW. J. Heterocycl. Chem. 1992, 29: 51 8b Player MR. Sowell JW. J. Heterocycl. Chem. 1993, 30: 125 9 Eger K. Lanzner W. Rothenhäusler K. Liebigs Ann. Chem. 1993, 465 10 Monge A. Palop J. Ramirez C. Font M. Fernandez-Alvarez E. Eur. J. Med. Chem. 1991, 26: 71 11 Becher J. Pluta K. Krake N. Brøndum K. Christensen NJ. Vinader MV. Synthesis 1989, 530 12 Aggarval V. Kumar A. Junjappa H. Synthesis 1981, 157 13 Alekseeva LM. Mukhanova TI. Panisheva EK. Anisimova OS. Turchin KF. Komkov AV. Dorokhov VA. Granik VG. Russ. Chem. Bull. 1999, 48: 160 14a Yamanaka H. Komatsu M. Tanji KI. Ogawa S. Konno S. Mizugaki M. Yakugaku Zashi 1979, 99: 342 ; Chem. Abstr. 1979, 91, 175289 14b Meyer H. Bossert F. Horstmann H. Liebigs Ann. Chem. 1977, 1895 15 Roth B. Smith JM. J. Am. Chem. Soc. 1949, 71: 616 16 Hojo M. Masuda R. Okada E. Yamamoto H. Morimoto K. Okada K. Synthesis 1990, 195 17 Troschütz R. Arch. Pharm. (Weinheim) 1989, 322: 285 18 Troschütz R. Lückel A. Arch. Pharm. (Weinheim) 1991, 324: 73 19a Allen GR. Pidacks C. Wein MJ. J. Am. Chem. Soc. 1966, 88: 2536 19b Patrick JB. Saunders EK. Tetrahedron Lett. 1979, 20: 4009 20 Jaime-Figuerusa S. Liu Y. Muchowski JM. Putman DG. Tetrahedron Lett. 1998, 39: 1313 21a Dorokhov VA. Gordeev MF. Bogdanov VS. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1988, 37: 1265 ; Chem. Abstr. 1988, 110, 57102 21b Dorokhov VA. G ordeev MF. Komkov AV. Bogdanov VS. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1990, 39: 340 22 Hirayama T, and Nagakawa K. inventors; Japanese Patent 50129576. ; Chem. Abstr. 1975, 84, 180257 23a Claisen L. Ber. Dtsch. Chem. Ges. 1892, 25: 1787 23b Claisen L. Ber. Dtsch. Chem. Ges. 1903, 36: 3364 24 Barret R. Daudon M. Tetrahedron Lett. 1990, 34: 4871 25a Shaikh IA. Johnson F. Grollman AP. J. Med. Chem. 1986, 29: 1329 25b Bock H. Dickmann P. Herrmann H.-F. Z. Naturforsch. B. 1991, 46: 326 26a Shaikh IA. Johnson F. Grollman AP. J. Med. Chem. 1986, 29: 1329 26b Potts KT. Bhattacharjee D. Walsh EB. J. Org. Chem. 1986, 51: 2011
