Synthesis of new active o-nitrophenyl carbamates

Synthetic Communications

Volumn 35, Issue 11, 2005, Pages 1471-1479

  Simon, Monika ^a   Csunderlik, Carol ^a   Cotarca, Livius ^b   Cǎproiu, Miron Teodor ^c   Neda, Ion ^d   Turoczi, Maria Cristina ^a   Volpicelli, Raffaella ^b  

^a POLITEHNICA UNIVERSITY OF TIMISOARA   (Romania)

^b Zambon Group SpA   (Italy)

^c INSTITUTE OF ORGANIC CHEMISTRY   (Romania)

^d InnoChemTech GmbH   (Germany)

Author keywords

Bis(o nitrophenyl) carbonate; O nitrophenyl carbamates; Phosgene free carbonylations; Triphosgene

Indexed keywords

BIS(2 NITROPHENYL)CARBONATE; CARBAMIC ACID DERIVATIVE; CARBONIC ACID DERIVATIVE; N BENZYL 2 NITROPHENYL CARBAMATE; N BUTYL 2 NITROPHENYL CARBAMATE; N CYCLOHEXYL 2 NITROPHENYL CARBAMATE; N ISOBUTYL 2 NITROPHENYL CARBAMATE; N ISOPENTHYL 2 NITROPHENYL CARBAMATE; N ISOPROPYL 2 NITROPHENYL CARBAMATE; N ISOPROPYL 4 NITROPHENYL CARBAMATE; N PROPYL 2 NITROPHENYL CARBAMATE; N PROPYL 4 NITROPHENYL CARBAMATE; N SEC BUTYL 2 NITROPHENYL CARBAMATE; N,N DIBENZYL 2 NITROPHENYL CARBAMATE; N,N DIISOBUTYL 2 NITROPHENYL CARBAMATE; N.N' DICYCLOHEXYLUREA; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; INFRARED RADIATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 20844460146     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1081/SCC-200057986     Document Type: Article

References (22)

1. Adams, P.; Baron, F. A. Esters of carbamic acid. Chem. Rev. 1965, 65, 596-597.
2. Ryan, T. A.; Ryan, C.; Seddon, E. A.; Seddon, K. R. Phosgene and Related Carbonyl Halide; Elsevier: Amsterdam, 1996; 205-208.
3. Cotarca, L.; Eckert, H. Topics on specific synthetic applications of phosgenation reactions. In Phosgenations - A Handbook; Wiley-VCH Verlag GmbH & Co. KgaA: Weinheim, 2003; 521-597.
4. Matyner, M.; Kurkjz, R. P.; Cotter, R. The chemistry of chloroformates. Reactions of chloroformates with nitrogen compounds. Chem. Rev. 1964, 64, 656-664.
5. Oyaki, S. Isocyanate chemistry. Reactions with alcohols and phenols. Chem. Rev. 1972, 72, 470-472.
6. Barton, D.; Ollis, W. D. Derivatives of carbon dioxide. In Comprehensive Organic Chemistry; Pergamon Press: Oxford, 1979; Vol. 2, 1083-1090.
7. (a) Kim, S.; Ko Kwan, Y. Convenient method for the preparation of active carbonates, active carbamates and ureas using di-2-pyridyl carbonate. Bull. Korean Chem. Soc. 1985, 6 (3), 175-1766;
8. (b) Ghosh, A. K.; Duond, T. T.; McKee, S. P. Di(2-pyridyl) carbonate promoted alkoxycarbonylation of amines: A convenient synthesis of functionalized carbamates. Tetrahedron Lett. 1991, 32 (34), 4251-4254.
9. (a) Takeda, K.; Akagi, Y.; Saiki, A.; Tsukahara, T.; Ogura, H. Convenient methods for synthses of active carbamates, ureas and nitrosoureas using N,N′-disuccinimido carbonate (DSC). Tetrahedron Lett. 1983, 24 (42), 4569-4572;
10. (b) Ghosh, A. K.; Duong, T. T.; McKee, S. P.; Thompson, W. J. N, N′-Disuccinimidyl carbonate: A useful reagent for alkoxycarbonylation of amines. Tetrahedron Lett. 1992, 33 (20), 2781-2784.
11. Izdebski, I.; Pawlok, D. A new Convenient method for the synthesis of symmetrical and unsymmetrical N,N′-disubstituted ureas. Synthesis 1989, 423-4255.
12. (a) Glatthard, R.; Matter, M. Neues, mildes verfahren zur herstellung von aktiven carbonsäureestern und deren Verwendung als acylierungsmittel. Helv. Chim. Acta 1963, 46, 795-804;
13. 1) derivate der kohlensäure in der peptidchemie. Ann. 1962, 655, 189-194.
14. Brunelle, D. J. Novel catalysis of o-nitrophenyl carbonates by p-dimethylamino-pyridine. Tetrahedron Lett. 1982, 23 (17), 1739-1742.
15. Simon, M.; Csunderlik, C.; Medeleanu, M. Theoretical study of conformation and reactivity in the class of carbonic acid diesters. Rev. Chim. 2003, 54 (4), 325-330.
16. (a) Brunelle, D. J. Transesterification chemistry: Low temperature reactions of o-nitrophenyl carbonates. Macromol. Reports 1991A28(Suppl. 2), 95-102;
17. (b) Brunelle, D. J.; Shannon, T. G. Preparation and polymerization of bisphenol a cyclic oligomeric carbonates. Macromolecules 199124, 3035-3044.
18. Simon, M.; Csunderlik, C.; Medeleanu, M.; Dinache, A. Reactivity of bis(mononitrophenyl) carbonates in reactions with nitrogen nucleophiles and in basic hydrolysis. Rev. Chim. 200253 (7), 535-539.
19. Simon, M.; Csunderlik, C.; Jones, P. G.; Neda, I.; Fischer, A. K. A second polymorph of bis(o-nitrophenyl) carbonate. Acta Cryst. 2003.E59, o688-o690.
20. Simon, M.; Csunderlik, C.; Tirnaveanu, A. Preparation of bis(mononitrophenyl) carbonates from triphosgene and nitrophenols. Rev. Chim. 200152 (7-8), 371-376.
21. Johnston, T. P.; Kussner, C. L.; Carter, R. L.; Frye, J. L.; Lomax, N. R.; Plowman, J.; Narazanan, V. L. Studies on synthesis and anticancer activity of selected N-(2-fluoroethyl)-N-nitrosoureas. J. Med. Chem. 198427, 1422-1426.
22. Skita, A.; Rolfes, H. Über cyclohexylamine (II). Ber. Dtsch. Chem. Ges. 192053, 1242-1255.