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
References
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.300
16 Bruker Molecular Analysis Research
Tool V 5.625, 1997 -2000 ,
Bruker AXS.
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
18 Sheldrick, G. M.; SHELXL97: Program
for Crystal Structure Refinement, Institut für Anorganische
Chemie der Universität Göttingen, Göttingen,
Germany.