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DOI: 10.1055/s-2001-17705
Synthesis of New Stereoisomeric Nitrate Esters Derived from Isosorbide-Mononitrate II: Bicyclic δ-Lactams and Tetrahydrofuran Derivatives
Publication History
Publication Date:
11 August 2004 (online)
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Abstract
The synthesis of the diastereomeric nitrate esters (3R,4R)-(2-hydroxy-4-nitrooxytetrahydrofuran-3-yloxy)acetonitrile (5b) and (3R,4S)-(2-hydroxy-4-nitrooxytetrahydrofuran-3-yloxy)acetonitrile (9) was achieved by the Beckmann fragmentation of 1,4:3,6-dianhydro-d-glucitol-5-(or -2-)nitrate-2-(or -5-)ketoximes (4b and 8), respectively. The bicyclic δ-lactams, (1R,6R,7R)-N-methyl-7-endo-nitrooxy-3-oxo-5,9-dioxa-2-azabicyclo[4.3.0]nonane (15b) and the stereoisomer (1R,6R,7S)-7-exo-nitrooxy-3-oxo-5,9-dioxa-2-azabicyclo[4.3.0]nonane (18b) were prepared by the Beckmann rearrangement of nitrones 14b and 17b, respectively. The stereoisomeric δ-lactams, N-methyl-7-endo-benzoyloxy- (15a) and N-methyl-7-exo-benzoyloxy-3-oxo-5,9-dioxa-2-azabicyclo[4.3.0]nonane (18a) were prepared from the corresponding nitrones 14a and 17a, respectively.
Key words
heterocycles - nitrones - isosorbide ketonitrates - δ-lactams - Beckmann rearrangement
-
1a
Abshagen U.Sporel-Radum S. Eur. J. Clin. Pharmacol. 1981, 19: 423 -
1c
Sandrock K, andGunter C. inventors; German Patent 2 903 927. -
1e
Stoss P. inventors; German Patent 3 124 410. - 2
Stoss P.Hemmer R. Adv. Carbohydrate Chem. and Biochem. 1991, 49: 93 and references cited therein -
3a
Schneider W.Stahl B.Kaltenbach M.Bussmann WD. Arzneim.-Forsch./Drug Res. 1984, 34 (II): 1779 -
3b
Wood G.John BA.Chasseaud LF.Major RM.Forrest ME.Bonn R.Lambe RF.Darragh A. Arzneim.-Forsch./Drug Res. 1984, 34 (II): 1031 -
4a
Fleche G.Huchete M. Starch/Starke 1986, 38: 26 -
4b
Cekovic -
4c
Dosen-Mi Lj.covic Cekovic -
4d
Wiggins LF. Adv. Carbohydrate. Chem. 1950, 5: 191 -
4e
Barker J. J. Org. Chem. 1970, 35: 461 -
5a
Brimacombe JS.Foster AB.Stacey M.Whiffen DH. Tetrahedron 1958, 4: 351 -
5b
Szeja W. J. Chem. Soc., Chem. Commun. 1981, 215 -
5c
Lemieux RU.McInnes AG. Can. J. Chem. 1960, 38: 136 -
5d
Buck KW.Duxbury JM.Foster AB.Perry AR.Webber JM. Carbohydr. Res. 1966, 2: 122 -
6a
Urones JG.Marcos IS.Garrido NM.Basabe P.San Feliciano SG.Coca R.Diez D. Synlett. 1998, 1364 -
6b
Hayashi H.Keolo JI.Kubo K.Mokiyama J.Karasama A.Suzuki F. Chem. Pharm. Bull. 1993, 41: 1100 -
6c
Chao Q.Zhang J.Pickening TS.Jahanade M.Nair V. Tetrahedron 1998, 54: 3113 -
6d
Tamion R.Marsais F.Ribereau P.Queguiner G. Tetrahedron: Asymmetry 1993, 4: 2415 -
6e
Tamion R.Marsais F.Ribereau P.Queguiner G.Abenhaim D.Loupy A.Munnier L. Tetrahedron: Asymmetry 1993, 4: 1879 -
6f
Tamion R.Marsais F.Queguiner G. Tetrahedron Lett. 1995, 36: 2761 -
6g
Paolucci C.Mazzini C.Fova A. J. Org. Chem. 1995, 60: 169 -
7a
Čeković Ž.Tokić-Vujošević Z. J. Serb. Chem. Soc. 1994, 59: 3 -
7b
Tokić-Vujošević Z.Čeković Ž. Heterocycl. Commun. 2001, 7: 43 - 8
Gawley RE. Org, React. 1988, 35: 1 ; and references cited therein -
9a
Marshall JA.Andersen NH.Schlicher JW. J. Org. Chem. 1970, 35: 858 -
9b
Seebach D.Pohmakotr M.Schregenberger C.Weidmann B.Mali RS.Pohmakotr S. Helv. Chim. Acta 1982, 65: 419 -
9c
Palmere RM.Conley RT.Rabinowitz JL. J. Org. Chem. 1972, 37: 4095 -
10a
Grob CA.Fischer HP.Raudenbusch W. Helv. Chim. Acta 1964, 47: 1003 -
10b
Fischer HP. Tetrahedron Lett. 1968, 285 -
10c
Hugel G.Gourdier B.Levy J.Le Men J. Tetrahedron Lett. 1974, 1597 -
10d
Morzycki JW.Jurek J.Rodewald WJ. Can. J. Chem. 1986, 64: 1540 -
10e
Achini R. Helv. Chim. Acta 1981, 64: 2203 -
11a
Barton DHR.Day MJ.Hesse RH.Pechet MM. J. Chem. Soc., Chem. Commun. 1971, 945 -
11b
Barton DHR.Day MJ.Hesse RH.Pechet MM. J. Chem. Soc., Perkin Trans. 1 1975, 1764 -
11c
Jeffs PW.Molina G.Cortese NA.Hanack PR.Wolfram J. J. Org. Chem. 1982, 47: 3876 -
11d
McMurry JE.Farina V.Scott WJ.Davidson AH.Summers DR.Shenvi A. J. Org. Chem. 1984, 49: 3803 - 12 Carbohydrate names for all compounds possessing sugar framework were used; however, in Beckmann rearrangement and fragmentation reactions considerable structural changes occur and we considered and named 5, 6 and 9 as heterocyclic compounds and δ-lactams 15 and 18 as bridged bicyclic systems.
-
13a C
ekovic Tokic Z. Synthesis 1989, 610 -
13b
Stoss P.Merrath P.Schluter G. Synthesis 1987, 174 -
14a C
ekovi c Tokic Z. J. Serb. Chem. Soc. 1994, 59: 3 -
14b
Andersson F.Samuelsson B. Carbohydrate Res. 1984, C1: 129 -
14c
Corey EJ.Schmidth G. Tetrahedron Lett. 1979, 5: 399