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DOI: 10.1055/s-2002-35987
Studies on Isocyanides and Related Compounds; Synthesis of 1,4-Benzodiazepine-2,5-diones via Ugi Four-Component Condensation
Publikationsverlauf
Publikationsdatum:
06. Dezember 2002 (online)
Abstract
A convenient two-step synthesis of the title compounds based on the isocyanide chemistry is reported. The Ugi four-component condensation between 4-chloro-2-nitrobenzoic acid (1), aldehydes 2, cyclohexyl isocyanide (3) and α-amino esters as the amino components afforded the expected nitro compounds 5 which were reductively cyclized to the desired 1,4-benzodiazepine-2,5-diones 7 via the intermediate amino derivatives 6.
Key words
heterocycles - cyclizations - diastereoselectivity - condensation - benzodiazepine - isocyanides
- 1a
Wright WB.Brabander HJ.Greenblatt EN.Day IP.Hardy RA. J. Med. Chem. 1978, 21: 1087 - 1b
McDowell RS.Blackburn BK.Gadek TR.McGee LR.Rawson T.Reynolds ME.Robarge KD.Somers TC.Thorsett ED.Tischler M.Webb RR.Venuti MC. J. Am. Chem. Soc. 1994, 116: 5077 - 1c
Cho NS.Song KY.Párkányi C. J. Heterocycl. Chem. 1989, 26: 1807 - 1d
De Martino G.Massa S.Corelli F.Pantaleoni G.Fanini D.Palumbo G. Eur. J. Med. Chem.-Chim. Ther. 1983, 18: 347 - 1e
Jones GB.Davey CL.Jenkins TC.Kamal A.Kneale GG.Neidle S.Webster GD.Thurston DE. Anti-Cancer Drug Des. 1990, 5: 249 - 2a
Kaneko T.Wong H.Doyle TW. Tetrahedron Lett. 1983, 24: 5165 - 2b
Reed JN.Snieckus V. Tetrahedron Lett. 1984, 25: 5505 - 2c
Kamal A.Thurston DE. Tetrahedron Lett. 1989, 30: 6221 - 2d
Gu Z.-Q.Wong G.Dominguez C.de Costa BR.Rice KC.Skolnick P. J. Med. Chem. 1993, 36: 1001 - 3a
Kaneko T.Wong H.Doyle TW. J. Antibiot. 1984, 37: 300 - 3b
Confalone PN.Huie EM.Ko SS.Cole GM. J. Org. Chem. 1988, 53: 482 - 3c
Kamal A. J. Org. Chem. 1991, 56: 2237 - 3d
Karp GM. J. Org. Chem. 1995, 60: 5814 - 4
Mori M.Kimura M.Uozomi Y.Ban Y. Tetrahedron Lett. 1985, 26: 5947 - 5
Keating TA.Armstrong RW. J. Org. Chem. 1996, 61: 8935 - 6
Keating TA.Armstrong RW. J. Am. Chem. Soc. 1996, 118: 2574 - 7
Hulme C.Peng J.Tang S.-Y.Burns CJ.Morize I.Labaudiniere R. J. Org. Chem. 1998, 63: 8021 - 8
Hulme C.Peng J.Morton G.Salvino JM.Herpin T.Labaudiniere R. Tetrahedron Lett. 1998, 39: 7227 - 9 For a review, see:
Ugi I.Dömling A. Angew. Chem. Int. Ed. 2000, 39: 3168 - 10
Ugi IK.Eckert B.Hörl W. Chemosphere 2001, 43: 75 - 11
Chucholowski A.Heinrich D.Mathys B.Müller C. Abstr. Pap. Am. Chem. Soc. 1997, 214: 287 - 12
Rosendahl FK.Ugi I. Ann. Chem. 1963, 666: 65 - Review:
- 13a
Marcaccini S.Torroba T. Org. Prep. Proc. Int. 1993, 25: 141 - 13b
Bossio R.Marcaccini S.Pepino R. Synthesis 1994, 765 - 13c
Bossio R.Marcaccini S.Pepino R. Tetrahedron Lett. 1995, 36: 2325 - 13d
Bossio R.Marcaccini S.Pepino R. J. Heterocycl. Chem. 1995, 32: 1115 - 13e
Bossio R.Marcaccini S.Pepino R.Torroba T. J. Org. Chem. 1996, 61: 2202 - 13f
Bossio R.Marcaccini S.Pepino R.Torroba T. J. Chem. Soc., Perkin Trans. 1 1996, 229 - 13g
Bossio R.Marcaccini S.Pepino R.Torroba T. Heterocycles 1996, 43: 471 - 13h
Bossio R.Marcos CF.Marcaccini S.Pepino R. Heterocycles 1997, 45: 1589 - 13i
Bossio R.Marcaccini S.Pepino R.Torroba T. Heterocycles 1999, 50: 463 - 13j
Marcaccini S.Pepino R.Pozo MC. Tetrahedron Lett. 2001, 42: 2727 - 14
Gokel GW.Widera RP.Weber WP. Org. Synth. 1976, 55: 96 - 15
Ugi I.Meyr R.Lipinsky M.Bodesheim F.Rosendahl F. Org. Synth., Coll. Vol. 5 Wiley; London: 1973. p.300Reference Ris Wihthout Link - 17
Altomare A.Burla MC.Camalli M.Cascarano GL.Giacovazzo C.Guagliardi A.Moliterni AGG.Polidori G.Spagna R. J. Appl. Crystallogr. 1999, 32: 115
References
Bruker Molecular Analysis Research Tool V 5.625, 1997-2000, Bruker AXS.
18Sheldrick, G. M.; SHELXL97: Program for Crystal Structure Refinement, Institut für Anorganische Chemie der Universität Göttingen, Göttingen, Germany.