Expedient synthesis of 2-chloroethylnitrososulfamide (CENS) via the decarboxylative reopening of sulfanoyloxazolidinones

Tetrahedron Letters

Volumn 37, Issue 32, 1996, Pages 5695-5698

  Abdaoui, Mohamed ^a   Dewynter, Georges ^a   Montero, Jean Louis ^a  

^a NONE

Author keywords

alkylating agent; carbamoylsulfamide; carboxylsulfamide; chloration; chloroethylnitro sosulfamide; chlorosulfonyl isocyanate; decarboxylation; nitrosation; oncostatic; sulfamoyloxazolidino ne

Indexed keywords

ANTINEOPLASTIC AGENT; NITROSO DERIVATIVE; SULFAMIDE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030570862     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01195-1     Document Type: Article

References (29)

1. 1 Abdaoui, M.; Dewynter, G.; Aouf, N.; Favre, G.; Morere, A.; Montero, J-L. Biorg. Med. Chem. 1996, in press. Related papers concerning N-nitrososulfamates and Diazald® see White, E. H.; Min Li and Shanzheng Lu.J. Org. Chem. 1992,57, 1252-1258. de Boer, Th. J.; Backer, H. J. Rec. Trav. Chim. Pays-Bas 1954, 73, 229-233. de Boer Th. J.; Backer, H. J. Org. Synth. Coll. 1963, 4, 250-255.
2. 1 Abdaoui, M.; Dewynter, G.; Aouf, N.; Favre, G.; Morere, A.; Montero, J-L. Biorg. Med. Chem. 1996, in press. Related papers concerning N-nitrososulfamates and Diazald® see White, E. H.; Min Li and Shanzheng Lu.J. Org. Chem. 1992,57, 1252-1258. de Boer, Th. J.; Backer, H. J. Rec. Trav. Chim. Pays-Bas 1954, 73, 229-233. de Boer Th. J.; Backer, H. J. Org. Synth. Coll. 1963, 4, 250-255.
3. 1 Abdaoui, M.; Dewynter, G.; Aouf, N.; Favre, G.; Morere, A.; Montero, J-L. Biorg. Med. Chem. 1996, in press. Related papers concerning N-nitrososulfamates and Diazald® see White, E. H.; Min Li and Shanzheng Lu.J. Org. Chem. 1992,57, 1252-1258. de Boer, Th. J.; Backer, H. J. Rec. Trav. Chim. Pays-Bas 1954, 73, 229-233. de Boer Th. J.; Backer, H. J. Org. Synth. Coll. 1963, 4, 250-255.
4. 1 Abdaoui, M.; Dewynter, G.; Aouf, N.; Favre, G.; Morere, A.; Montero, J-L. Biorg. Med. Chem. 1996, in press. Related papers concerning N-nitrososulfamates and Diazald® see White, E. H.; Min Li and Shanzheng Lu.J. Org. Chem. 1992,57, 1252-1258. de Boer, Th. J.; Backer, H. J. Rec. Trav. Chim. Pays-Bas 1954, 73, 229-233. de Boer Th. J.; Backer, H. J. Org. Synth. Coll. 1963, 4, 250-255.
5. (c). Hudlicky, M. J. Org. Chem. 1980, 45, 5377-5378. For a review see: Sulfamic Acid and its N-substituted Derivatives. Benson, G. A.; Spillane, W. J. Chem. Rev. 1980, 80, 151-186.
6. (c). Hudlicky, M. J. Org. Chem. 1980, 45, 5377-5378. For a review see: Sulfamic Acid and its N-substituted Derivatives. Benson, G. A.; Spillane, W. J. Chem. Rev. 1980, 80, 151-186.
7. 2 For a general reviews concerning the clinical use and the pharmacological properties of CENU see Mc Cormick, I.E.; Mc Elhinney, R.S. Eur. J. Cancer 1990, 26, 207-221 (and ref. cit. therein). Carter, S. K.; Bakowski, M. T.; Hellman, K. Chemotherapy of Cancer 3rd ed.; Churchill Livingston: New York, 1987. Calabresi, P.; Schein, P. S.; Rosenberg, S.A. Eds. Medical Oncology Macmillan: New York. 1985. Eisenbrand, G. in Relevance of N-Nitroso Compounds to Human Cancer: exposure and Mechanisms Bartsch, H.; O'Neill, I. K.; Schulte-Herman, R. Eds; International Agency for Research on Cancer, Lyon, France, 1984.
8. 2 For a general reviews concerning the clinical use and the pharmacological properties of CENU see Mc Cormick, I.E.; Mc Elhinney, R.S. Eur. J. Cancer 1990, 26, 207-221 (and ref. cit. therein). Carter, S. K.; Bakowski, M. T.; Hellman, K. Chemotherapy of Cancer 3rd ed.; Churchill Livingston: New York, 1987. Calabresi, P.; Schein, P. S.; Rosenberg, S.A. Eds. Medical Oncology Macmillan: New York. 1985. Eisenbrand, G. in Relevance of N-Nitroso Compounds to Human Cancer: exposure and Mechanisms Bartsch, H.; O'Neill, I. K.; Schulte-Herman, R. Eds; International Agency for Research on Cancer, Lyon, France, 1984.
9. 2 For a general reviews concerning the clinical use and the pharmacological properties of CENU see Mc Cormick, I.E.; Mc Elhinney, R.S. Eur. J. Cancer 1990, 26, 207-221 (and ref. cit. therein). Carter, S. K.; Bakowski, M. T.; Hellman, K. Chemotherapy of Cancer 3rd ed.; Churchill Livingston: New York, 1987. Calabresi, P.; Schein, P. S.; Rosenberg, S.A. Eds. Medical Oncology Macmillan: New York. 1985. Eisenbrand, G. in Relevance of N-Nitroso Compounds to Human Cancer: exposure and Mechanisms Bartsch, H.; O'Neill, I. K.; Schulte-Herman, R. Eds; International Agency for Research on Cancer, Lyon, France, 1984.
10. 2 For a general reviews concerning the clinical use and the pharmacological properties of CENU see Mc Cormick, I.E.; Mc Elhinney, R.S. Eur. J. Cancer 1990, 26, 207-221 (and ref. cit. therein). Carter, S. K.; Bakowski, M. T.; Hellman, K. Chemotherapy of Cancer 3rd ed.; Churchill Livingston: New York, 1987. Calabresi, P.; Schein, P. S.; Rosenberg, S.A. Eds. Medical Oncology Macmillan: New York. 1985. Eisenbrand, G. in Relevance of N-Nitroso Compounds to Human Cancer: exposure and Mechanisms Bartsch, H.; O'Neill, I. K.; Schulte-Herman, R. Eds; International Agency for Research on Cancer, Lyon, France, 1984.
11. 3 Dewynter, G.; Montero, J-L. C-r. Acad. Sci. Paris. Ser II. 1992, 315, 1675-1682.
12. 4 Montero, J-L.; Dewynter, G.; Agoh, B.; Delaunay, B.; Imbach, J-L. Tetrahedron Lett, 1983, 24, 3091-3094. Bonnaud, B.; Viani, R.; Agoh, B.; Delaunay, B.; Dewynter, G.; Montero, J-L. Acta cryst. 1987, C-43, 2466-2468. Agoh, B.; Dewynter, G.; Montero, J-L.; Leydet, A.; Imbach, J-L. Bull. Soc Chim. Fr. 1987, 5, 867-872.
13. 4 Montero, J-L.; Dewynter, G.; Agoh, B.; Delaunay, B.; Imbach, J-L. Tetrahedron Lett, 1983, 24, 3091-3094. Bonnaud, B.; Viani, R.; Agoh, B.; Delaunay, B.; Dewynter, G.; Montero, J-L. Acta cryst. 1987, C-43, 2466-2468. Agoh, B.; Dewynter, G.; Montero, J-L.; Leydet, A.; Imbach, J-L. Bull. Soc Chim. Fr. 1987, 5, 867-872.
14. 4 Montero, J-L.; Dewynter, G.; Agoh, B.; Delaunay, B.; Imbach, J-L. Tetrahedron Lett, 1983, 24, 3091-3094. Bonnaud, B.; Viani, R.; Agoh, B.; Delaunay, B.; Dewynter, G.; Montero, J-L. Acta cryst. 1987, C-43, 2466-2468. Agoh, B.; Dewynter, G.; Montero, J-L.; Leydet, A.; Imbach, J-L. Bull. Soc Chim. Fr. 1987, 5, 867-872.
15. 2S).
16. 2: Scam, H.L.; Wideburg, N.E.; Spanton, S.G.; Kolhbrenner, W.E.; Betebenner, D.ZA.; Kempf, D.J.; Norbeck, D.W.; Plattner, J.J.; Erickson, J.W. J. Chem. Soc., Chem. Commun. 1991, 2, 110-112. Neutral hydrolysis: Monsanto USA Pat. 4810426, 1989]. The N-sulfonyloxazolidinone cleavage can be obtained under irradiation conditions [Li, C.; Fuchs, P.L. Tetrahedron Lett. 1993, 34, 1855-1858]; a related radical approach to N-desulfonylation was recently reported [Parsons, A.F.; Pettifer, R.M. Tetrahedron Lett. 1996, 37, 1667-1670] .
17. 2: Scam, H.L.; Wideburg, N.E.; Spanton, S.G.; Kolhbrenner, W.E.; Betebenner, D.ZA.; Kempf, D.J.; Norbeck, D.W.; Plattner, J.J.; Erickson, J.W. J. Chem. Soc., Chem. Commun. 1991, 2, 110-112. Neutral hydrolysis: Monsanto USA Pat. 4810426, 1989]. The N-sulfonyloxazolidinone cleavage can be obtained under irradiation conditions [Li, C.; Fuchs, P.L. Tetrahedron Lett. 1993, 34, 1855-1858]; a related radical approach to N-desulfonylation was recently reported [Parsons, A.F.; Pettifer, R.M. Tetrahedron Lett. 1996, 37, 1667-1670] .
18. 2: Scam, H.L.; Wideburg, N.E.; Spanton, S.G.; Kolhbrenner, W.E.; Betebenner, D.ZA.; Kempf, D.J.; Norbeck, D.W.; Plattner, J.J.; Erickson, J.W. J. Chem. Soc., Chem. Commun. 1991, 2, 110-112. Neutral hydrolysis: Monsanto USA Pat. 4810426, 1989]. The N-sulfonyloxazolidinone cleavage can be obtained under irradiation conditions [Li, C.; Fuchs, P.L. Tetrahedron Lett. 1993, 34, 1855-1858]; a related radical approach to N-desulfonylation was recently reported [Parsons, A.F.; Pettifer, R.M. Tetrahedron Lett. 1996, 37, 1667-1670] .
19. 2: Scam, H.L.; Wideburg, N.E.; Spanton, S.G.; Kolhbrenner, W.E.; Betebenner, D.ZA.; Kempf, D.J.; Norbeck, D.W.; Plattner, J.J.; Erickson, J.W. J. Chem. Soc., Chem. Commun. 1991, 2, 110-112. Neutral hydrolysis: Monsanto USA Pat. 4810426, 1989]. The N-sulfonyloxazolidinone cleavage can be obtained under irradiation conditions [Li, C.; Fuchs, P.L. Tetrahedron Lett. 1993, 34, 1855-1858]; a related radical approach to N-desulfonylation was recently reported [Parsons, A.F.; Pettifer, R.M. Tetrahedron Lett. 1996, 37, 1667-1670] .
20. 2: Scam, H.L.; Wideburg, N.E.; Spanton, S.G.; Kolhbrenner, W.E.; Betebenner, D.ZA.; Kempf, D.J.; Norbeck, D.W.; Plattner, J.J.; Erickson, J.W. J. Chem. Soc., Chem. Commun. 1991, 2, 110-112. Neutral hydrolysis: Monsanto USA Pat. 4810426, 1989]. The N-sulfonyloxazolidinone cleavage can be obtained under irradiation conditions [Li, C.; Fuchs, P.L. Tetrahedron Lett. 1993, 34, 1855-1858]; a related radical approach to N-desulfonylation was recently reported [Parsons, A.F.; Pettifer, R.M. Tetrahedron Lett. 1996, 37, 1667-1670] .
21. 2: Scam, H.L.; Wideburg, N.E.; Spanton, S.G.; Kolhbrenner, W.E.; Betebenner, D.ZA.; Kempf, D.J.; Norbeck, D.W.; Plattner, J.J.; Erickson, J.W. J. Chem. Soc., Chem. Commun. 1991, 2, 110-112. Neutral hydrolysis: Monsanto USA Pat. 4810426, 1989]. The N-sulfonyloxazolidinone cleavage can be obtained under irradiation conditions [Li, C.; Fuchs, P.L. Tetrahedron Lett. 1993, 34, 1855-1858]; a related radical approach to N-desulfonylation was recently reported [Parsons, A.F.; Pettifer, R.M. Tetrahedron Lett. 1996, 37, 1667-1670] .
22. 2: Scam, H.L.; Wideburg, N.E.; Spanton, S.G.; Kolhbrenner, W.E.; Betebenner, D.ZA.; Kempf, D.J.; Norbeck, D.W.; Plattner, J.J.; Erickson, J.W. J. Chem. Soc., Chem. Commun. 1991, 2, 110-112. Neutral hydrolysis: Monsanto USA Pat. 4810426, 1989]. The N-sulfonyloxazolidinone cleavage can be obtained under irradiation conditions [Li, C.; Fuchs, P.L. Tetrahedron Lett. 1993, 34, 1855-1858]; a related radical approach to N-desulfonylation was recently reported [Parsons, A.F.; Pettifer, R.M. Tetrahedron Lett. 1996, 37, 1667-1670] .
23. 2: Scam, H.L.; Wideburg, N.E.; Spanton, S.G.; Kolhbrenner, W.E.; Betebenner, D.ZA.; Kempf, D.J.; Norbeck, D.W.; Plattner, J.J.; Erickson, J.W. J. Chem. Soc., Chem. Commun. 1991, 2, 110-112. Neutral hydrolysis: Monsanto USA Pat. 4810426, 1989]. The N-sulfonyloxazolidinone cleavage can be obtained under irradiation conditions [Li, C.; Fuchs, P.L. Tetrahedron Lett. 1993, 34, 1855-1858]; a related radical approach to N-desulfonylation was recently reported [Parsons, A.F.; Pettifer, R.M. Tetrahedron Lett. 1996, 37, 1667-1670] .
24. ]+).
25. 8 Oiry, J.; Imbach, J-L. Eur. J. Med. Chem.; 1984, 19, 305-310. Oiry, J.; Pompon, A.; Madelmont, J-C.; Imbach, J-L. ibid, p 311-314. Maral, R.; Bourrut, C.; Chenut, E.; Mathé, G.; Imbach, J-L. ibid, p 315-319. Maral, R.; Mathé, G.; Schein, P.S.; Bourrut, C.; Chenut, E.; Oiry, J.; Imbach, J-L. Exptl. Clin. Res. 1984,12, 883-886. Oiry, J.; Imbach, J-L. Eur pat. 834 010 795 1983 and US pat.499 130 1983.
26. 8 Oiry, J.; Imbach, J-L. Eur. J. Med. Chem.; 1984, 19, 305-310. Oiry, J.; Pompon, A.; Madelmont, J-C.; Imbach, J-L. ibid, p 311-314. Maral, R.; Bourrut, C.; Chenut, E.; Mathé, G.; Imbach, J-L. ibid, p 315-319. Maral, R.; Mathé, G.; Schein, P.S.; Bourrut, C.; Chenut, E.; Oiry, J.; Imbach, J-L. Exptl. Clin. Res. 1984,12, 883-886. Oiry, J.; Imbach, J-L. Eur pat. 834 010 795 1983 and US pat.499 130 1983.
27. 8 Oiry, J.; Imbach, J-L. Eur. J. Med. Chem.; 1984, 19, 305-310. Oiry, J.; Pompon, A.; Madelmont, J-C.; Imbach, J-L. ibid, p 311-314. Maral, R.; Bourrut, C.; Chenut, E.; Mathé, G.; Imbach, J-L. ibid, p 315-319. Maral, R.; Mathé, G.; Schein, P.S.; Bourrut, C.; Chenut, E.; Oiry, J.; Imbach, J-L. Exptl. Clin. Res. 1984,12, 883-886. Oiry, J.; Imbach, J-L. Eur pat. 834 010 795 1983 and US pat.499 130 1983.
28. 8 Oiry, J.; Imbach, J-L. Eur. J. Med. Chem.; 1984, 19, 305-310. Oiry, J.; Pompon, A.; Madelmont, J-C.; Imbach, J-L. ibid, p 311-314. Maral, R.; Bourrut, C.; Chenut, E.; Mathé, G.; Imbach, J-L. ibid, p 315-319. Maral, R.; Mathé, G.; Schein, P.S.; Bourrut, C.; Chenut, E.; Oiry, J.; Imbach, J-L. Exptl. Clin. Res. 1984,12, 883-886. Oiry, J.; Imbach, J-L. Eur pat. 834 010 795 1983 and US pat.499 130 1983.
29. 8 Oiry, J.; Imbach, J-L. Eur. J. Med. Chem.; 1984, 19, 305-310. Oiry, J.; Pompon, A.; Madelmont, J-C.; Imbach, J-L. ibid, p 311-314. Maral, R.; Bourrut, C.; Chenut, E.; Mathé, G.; Imbach, J-L. ibid, p 315-319. Maral, R.; Mathé, G.; Schein, P.S.; Bourrut, C.; Chenut, E.; Oiry, J.; Imbach, J-L. Exptl. Clin. Res. 1984,12, 883-886. Oiry, J.; Imbach, J-L. Eur pat. 834 010 795 1983 and US pat.499 130 1983.