Abstract
A number of protected 2-substituted 5,6,7,8-tetrahydro-5,8-methanoquinazoline-6,7-diols were prepared by condensation of amidines with (±)-exo ,exo -5,6-(isopropylidenedioxy)-3-(pyrrolidinomethylene)bicyclo[2.2.1]heptan-2-one. Deprotection of the 2-phenyl derivative was followed by its one-pot transformation into a 1:1 mixture of (±)-cis - and (±)-trans -2-phenyl-6,7-dihydro-5H -cyclopenta[d ]pyrimidine-5,7-dimethanol by oxidative glycol cleavage and subsequent reduction with sodium borohydride.
Key words
cyclocondensation - acetonide cleavage - oxidative cleavage - heterocycles - pyrimidine derivatives
References
1 De Clercq E.
Nat. Rev. Drug Discovery
2002,
1:
13
2 Crimmins MT.
Tetrahedron
1998,
54:
9229
3 Agrofoglio LS.
Challand R.
Acyclic, Carbocyclic and
-Nucleosides
Kluwer;
Dordrecht:
1998.
p.1-320
4 Agrofoglio L.
Suhas E.
Farese A.
Condom R.
Challand SR.
Guedj R.
Tetrahedron
1994,
50:
10611
5 Zhu XF.
Nucleosides, Nucleotides Nucleic Acids
2000,
19:
651
6 García MD.
Caamaño O.
Fernández F.
López MC.
De Clercq E.
Synthesis
2005,
925
7 García MD.
Caamaño O.
Fernández F.
Abeijón P.
Blanco JM.
Synthesis
2006,
73
8 Saksena AK.
McPhail AT.
Onan KD.
Tetrahedron Lett.
1981,
22:
2067
9 García MD.
Caamaño O.
Fernández F.
Figueira MJ.
Gómez G.
Synthesis
2003,
2138
10 Nagai S.
Ueda T.
Nagatsu A.
Nakaoka K.
Murakami N.
Sakakibara J.
Fujita M.
Hotta Y.
J. Heterocycl. Chem.
1998,
35:
329
11 Bellassoued-Fargeau M.-C.
Graffe B.
Sacquet MC.
Maitte P.
Heterocycles
1986,
24:
2831
12 Shoji F.
Eiko I.
Keiji K.
Toshifumi N.
Mitsuru S.
J. Med. Chem.
2002,
45:
3009
13 Mosti L.
Menozzi G.
Schenone P.
J. Heterocycl. Chem.
1983,
20:
649
14 Matsumoto T.
Watanabe M.
Mataka S.
Thiemann T.
Steroids
2003,
68:
751
15 Allen MP, Coe JW, Liras S, O’Donnell CJ, and O’Neill BT. inventors; US Patent Appl. 2005020830.
16 Cookson RC.
Dudfield PJ.
J. Chem. Soc., Perkin Trans. 1
1996,
393
17 Xiao X.
Bai D.
Synlett
2001,
535
18 Jähnisch K.
Tetrahedron Lett.
1997,
38:
227
19 Tulshian D.
Doll RJ.
Stansberry MF.
J. Org. Chem.
1991,
56:
6819
20 Zhu W.
Gumina G.
Shinazi F.
Chu CK.
Tetrahedron
2003,
59:
6423
21 Yang M.
Yei W.
Schneller SW.
J. Org. Chem.
2004,
69:
3993
22 Kinder FR.
Wattanasin S.
Versace RW.
Bair KW.
Bontempo J.
Green MA.
Lu YJ.
Marepalli R.
Phillips PE.
Roche D.
Tran LD.
Wang RM.
Waykole L.
Xu DD.
Zabludoff S.
J. Org. Chem.
2001,
66:
2118
23 Dumas M.
Vo-Quang Y.
Vo-Quang L.
Le Goffic F.
Synthesis
1989,
64
24 Caamaño O.
Gómez G.
Fernández F.
García MD.
García-Mera X.
De Clercq E.
Synthesis
2004,
2855
25 Anisotropy of the protons of the endocyclic methylene group of the trans -isomer arises from different intramolecular interactions of the hydroxymethylene groups.
