Abstract
Spiro(imidazolidinoquinazolinones), obtained easily in one step from 1-carbamoylisatins, are readily converted in three steps by successive N-alkylations and sodium borohydride regioselective reduction into the corresponding hydroxyspirolactams. The latter are valuable platforms for further transformations via the intermediacy of N -acyliminium species and have been applied to the synthesis of original isoquinoloquinazoline, indoloquinazoline and imidazoindole derivatives.
Key words
π-cyclisation - cleavage -
N -acyliminium ion - hydroxy lactam - reduction - imidazolidine - quinazolinone
References 1 Present address: CEA Saclay, INSTN-UESMS, 91191 Gif sur Yvette Cedex, France
2a Bergman J.
The Alkaloids
1983,
21:
29
2b Michael JP.
Nat. Prod. Rep.
2000,
17:
603
2c Michael JP.
Nat. Prod. Rep.
2001,
18:
543
2d Witt A.
Bergman J.
Curr. Org. Chem.
2003,
7:
659
3a da Silva JFM.
Garden SJ.
Pinto AC.
J. Braz. Chem. Soc.
2001,
12:
273
3b Reddy PS.
Vasantha T.
Heterocycles
2003,
60:
183
3c Hamid A.
Elomri A.
Daïch A.
Tetrahedron Lett.
2006,
47:
1777 ; and references cited therein
3d Carpenter RD.
Lam KS.
Kurth MJ.
J. Org. Chem.
2007,
72:
284
4a Hennequin LF.
Thomas AP.
Johnstone C.
Stokes ESE.
Plé PA.
Lohmann J.-JM.
Ogilvie DJ.
Dukes M.
Wedge SR.
Curwen JO.
Kendrew J.
van der Brempt CL.
J. Med. Chem.
1999,
42:
5369
4b Ferrini S.
Ponticelli F.
Taddei M.
Org. Lett.
2007,
9:
69 ; and references cited therein
4c Martínez-Vitturro CM.
Domínguez D.
Tetrahedron Lett.
2007,
48:
1023
5a Jones TR.
Thornton TJ.
Flinn A.
Jackman AL.
Newell DR.
Calvert AH.
J. Med. Chem.
1989,
32:
847
5b Malawska B.
Curr. Top. Med. Chem.
2005,
5:
69 ; and references cited therein
6 Kune J.
Bazant J.
Pour M.
Waisser K.
losárek M.
Janota J.
Farmaco
2000,
55:
725
7 Meyer MD.
Altenbach RJ.
Bai H.
Basha FZ.
Carroll WA.
Kerwin JF.
Lebold SA.
Lee E.
Pratt JK.
Sippy KB.
Tietje K.
Wendt MD.
Brune ME.
Buckner SA.
Hancock AA.
Drizin I.
J. Med. Chem.
2001,
44:
1971
8a Hasegawa H.
Muraoka M.
Matsui K.
Kojima A.
Bioorg. Med. Chem. Lett.
2003,
13:
3471
8b Hasegawa H.
Muraoka M.
Ohmori M.
Matsui K.
Kojima A.
Bioorg. Med. Chem.
2005,
13:
3721
8c Hasegawa H.
Muraoka M.
Ohmori M.
Matsui K.
Kojima A.
Chem. Pharm. Bull.
2005,
53:
1236
9 Pesquet A.
Daïch A.
Van Hijfte L.
J. Org. Chem.
2006,
71:
5303
10a Carrera JM.
Garvey DS.
J. Heterocycl. Chem.
1992,
29:
847
10b Liao Z.-K.
Kohn H.
J. Org. Chem.
1985,
50:
1884 ; and references cited therein from the same authors
10c Marquez VE.
Twanmoh L.-M.
Wood HB.
Driscoll JS.
J. Org. Chem.
1978,
37:
2558
11a Yamagishi M.
Ozaki KI.
Yamada Y.
Da-Te T.
Okamura K.
Suzuki M.
Chem. Pharm. Bull.
1991,
39:
1694
11b Yamagishi M.
Yamada Y.
Ozaki KI.
Asao M.
Shimizu R.
Suzuki M.
Matsumoto M.
Matsuoka Y.
Matsumoto K.
J. Med. Chem.
1992,
35:
2085
12a Daïch A.
Marchalín .
Pigeon P.
Decroix B.
Tetrahedron Lett.
1998,
39:
9187
12b Chihab-Eddine A.
Daïch A.
Jilale A.
Decroix B.
Tetrahedron Lett.
2001,
42:
573
12c Chihab-Eddine A.
Daïch A.
Jilale A.
Decroix B.
Heterocycles
2002,
58:
449
13 Hucher N.
Decroix B.
Daïch A.
Org. Lett.
2000,
2:
1201
14a Hucher N.
Decroix B.
Daïch A.
J. Org. Chem.
2001,
66:
4695
14b Cul A.
Chihab-Eddine A.
Pesquet A.
Marchalín .
Daïch A.
J. Heterocycl. Chem.
2003,
40:
499
14c Fogain-Ninkam A.
Daïch A.
Decroix B.
Netchitaïlo P.
Eur. J. Org. Chem.
2003,
4273
14d Hucher N.
Pesquet A.
Netchitaïlo P.
Daïch A.
Eur. J. Org. Chem.
2005,
2758
15 Pesquet A.
Daïch A.
Decroix B.
Van Hijfte L.
Org. Biomol. Chem.
2005,
3:
3937
16a Yamagishi M.
Ozaki KI.
Ohmizu H.
Yamada Y.
Suzuki M.
Chem. Pharm. Bull.
1990,
38:
2926
16b Yamagishi M.
Yamada Y.
Ozaki KI.
Tani J.
Suzuki M.
Chem. Pharm. Bull.
1991,
39:
626
16c Yamagishi M.
Ozaki KI.
Yamada Y.
Da-Te T.
Okamura K.
Suzuki M.
Chem. Pharm. Bull.
1991,
39:
1694
17 Yamagishi M.
Yamada Y.
Ozaki KI.
Asao M.
Shimizu R.
Suzuki M.
Matsumoto M.
Matsuoka Y.
Mataumoto K.
J. Med. Chem.
1992,
35:
2085
18a Kohn H.
Liao Z.-K.
J. Org. Chem.
1982,
47:
2787
18b Liao Z.-K.
Kohn H.
J. Org. Chem.
1984,
49:
3812
18c Liao Z.-K.
Kohn H.
J. Org. Chem.
1984,
49:
4745
18d Salazar L.
Rubido J.
Espada M.
Pedregal C.
Trigo G.
Elguero J.
J. Heterocycl. Chem.
1986,
23:
481
18e Yamagishi M.
Yamada Y.
Ozaki KI.
Da-Te T.
Okamura K.
Suzuki M.
Mataumoto K.
J. Org. Chem.
1992,
57:
1568
19 Full crystallographic data have been deposited at the Cambridge Crystallographic Data Centre; CCDC reference number 637457 for product 10b . Copies of the data can be obtained free of charge at the following address:
