메뉴 건너뛰기




Volumn 35, Issue 12, 2005, Pages 1663-1674

Expeditious method for synthesis of symmetrical 1,3-disubstituted ureas and thioureas

Author keywords

1,3 Disubstituted ureas; Diisocynates; Isocyanates; Tertiary amines; Thioisocyanates

Indexed keywords

1,3 DIALLYLUREA; 1,3 DIBENZYLTHIOUREA; 1,3 DIBENZYLUREA; 1,3 DIETHYLTHIOUREA; 1,3 DIETHYLUREA; 2,6 DIMETHYLPYRIDINE; AMINE; CARBANILIDE; ISOCYANIC ACID DERIVATIVE; ISOTHIOCYANIC ACID DERIVATIVE; PYRIDINE; THIOCARBANILIDE; THIOUREA DERIVATIVE; TRIETHYLAMINE; UNCLASSIFIED DRUG; UREA DERIVATIVE;

EID: 21044454077     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-200061656     Document Type: Article
Times cited : (40)

References (40)
  • 4
    • 0001329407 scopus 로고
    • Molecular scaffolds 3. An artificial parallel β-sheet
    • (a) Nowick, J. S.; Smith, E. M.; Noronha, G. Molecular scaffolds 3. An artificial parallel β-sheet. J. Org. Chem. 1995, 60, 7386-7387;
    • (1995) J. Org. Chem. , vol.60 , pp. 7386-7387
    • Nowick, J.S.1    Smith, E.M.2    Noronha, G.3
  • 5
    • 0029975981 scopus 로고    scopus 로고
    • Triurea derivatives of diethylenetriamine as potential templates for the formation of artificial β-sheets
    • (b) Nowick, J. S.; Mahrus, S.; Smith, E. M.; Ziller, J. W. Triurea derivatives of diethylenetriamine as potential templates for the formation of artificial β-sheets. J. Am. Chem. Soc. 1996, 118, 1066-1072;
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 1066-1072
    • Nowick, J.S.1    Mahrus, S.2    Smith, E.M.3    Ziller, J.W.4
  • 6
    • 0029670181 scopus 로고    scopus 로고
    • An artificial β-sheet comprising a molecular scaffold, a β-strand mimic and a peptide strand
    • (c) Nowick, J. S.; Holmes, D. L.; Mackin, G.; Noronha, G.; Shaka, A. J.; Smith, E. M. An artificial β-sheet comprising a molecular scaffold, a β-strand mimic and a peptide strand. J. Am. Chem. Soc. 1996, 118, 2764-2765;
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 2764-2765
    • Nowick, J.S.1    Holmes, D.L.2    Mackin, G.3    Noronha, G.4    Shaka, A.J.5    Smith, E.M.6
  • 7
    • 0030883636 scopus 로고    scopus 로고
    • Solid-phase synthesis of artificial β-sheets
    • (d) Holmes, D. H.; Smith, E. M.; Nowick, J. S. Solid-phase synthesis of artificial β-sheets. J. Am. Chem. Soc. 1997, 119, 7665-7669.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 7665-7669
    • Holmes, D.H.1    Smith, E.M.2    Nowick, J.S.3
  • 8
    • 0000517240 scopus 로고
    • Solid-phase synthesis on unnatural biopolymers containing repeating urea units
    • (a) Burgess, K.; Linthicum, D. S.; Shin, H. Solid-phase synthesis on unnatural biopolymers containing repeating urea units. Angew. Chem., Int. Ed. Engl. 1995, 34, 907-909;
    • (1995) Angew. Chem., Int. Ed. Engl. , vol.34 , pp. 907-909
    • Burgess, K.1    Linthicum, D.S.2    Shin, H.3
  • 11
    • 0030598062 scopus 로고    scopus 로고
    • Synthesis of a cyclic urea as a nonnatural biopolymer scaffold
    • (d) Kim, J.-M.; Wilson, T. E.; Norman, T. C.; Schultz, P. G. Synthesis of a cyclic urea as a nonnatural biopolymer scaffold. Tetrahedron Lett. 1996, 37, 5309-5312;
    • (1996) Tetrahedron Lett. , vol.37 , pp. 5309-5312
    • Kim, J.-M.1    Wilson, T.E.2    Norman, T.C.3    Schultz, P.G.4
  • 12
    • 0030764541 scopus 로고    scopus 로고
    • Approaches to the synthesis of ureapeptoide peptidomimetics
    • (e) Kruijtzer, J. A. W.; Lefeber, D. J.; Liskamp, R. M. J. Approaches to the synthesis of ureapeptoide peptidomimetics. Tetrahedron Lett. 1997, 38, 5335-5338;
    • (1997) Tetrahedron Lett. , vol.38 , pp. 5335-5338
    • Kruijtzer, J.A.W.1    Lefeber, D.J.2    Liskamp, R.M.J.3
  • 13
    • 0032505197 scopus 로고    scopus 로고
    • An efficient synthesis of N,N′-linked oligoureas
    • (f) Wilson, M. E.; Nowick, J. S. An efficient synthesis of N,N′-linked oligoureas. Tetrahedron Lett. 1998, 39, 6613-6616.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 6613-6616
    • Wilson, M.E.1    Nowick, J.S.2
  • 18
    • 33751157494 scopus 로고
    • A safe and efficient method for preparation of N, N′- unsymmetrically disubstituted ureas utilizing triphosgene
    • (a) Majer, P.; Randad, R. S. A safe and efficient method for preparation of N, N′-unsymmetrically disubstituted ureas utilizing triphosgene. J. Org. Chem. 1994, 59, 1937-1938;
    • (1994) J. Org. Chem. , vol.59 , pp. 1937-1938
    • Majer, P.1    Randad, R.S.2
  • 19
    • 0000631409 scopus 로고    scopus 로고
    • Phosgenated p-nitro phenyl (polystyrene) ketoxime or phoxime resin. A new resin for the solid-phase synthesis of ureas via thermolytic cleavage of oxime-carbamates
    • (b) Scialdone, M. A.; Shuey, S. W.; Soper, P.; Hamuro, Y.; Burns, D. M. Phosgenated p-nitro phenyl (polystyrene) ketoxime or phoxime resin. A new resin for the solid-phase synthesis of ureas via thermolytic cleavage of oxime-carbamates. J. Org. Chem. 1998, 63, 4802-4807;
    • (1998) J. Org. Chem. , vol.63 , pp. 4802-4807
    • Scialdone, M.A.1    Shuey, S.W.2    Soper, P.3    Hamuro, Y.4    Burns, D.M.5
  • 20
    • 49049127243 scopus 로고
    • Convenient methods for synthesis of active carbamates, ureas and nitrosoureas using N, N′-disuccinimido carbonates (DSC)
    • (c) Takeda, K.; Akagi, Y.; Saiki, A.; Tsukahara, T.; Ogura, H. Convenient methods for synthesis of active carbamates, ureas and nitrosoureas using N, N′-disuccinimido carbonates (DSC). Tetrahedron Lett. 1983, 24, 4569-4572;
    • (1983) Tetrahedron Lett. , vol.24 , pp. 4569-4572
    • Takeda, K.1    Akagi, Y.2    Saiki, A.3    Tsukahara, T.4    Ogura, H.5
  • 21
    • 85082702911 scopus 로고
    • A new convenient method for the synthesis of symmetrical and unsymmetrical N, N′-disubstituted ureas
    • (d) Izdebski, J.; Pawlak, D. A new convenient method for the synthesis of symmetrical and unsymmetrical N, N′-disubstituted ureas. Synthesis 1989, 6, 423-425;
    • (1989) Synthesis , vol.6 , pp. 423-425
    • Izdebski, J.1    Pawlak, D.2
  • 22
    • 0000747972 scopus 로고    scopus 로고
    • Formation of urea dipeptides from carbonyldiimidazole: Application toward the protease inhibitors GE20372 and MAPI
    • (e) Zhang, X.; Rodrigues, J.; Evans, L.; Hinckle, B.; Ballantyne, L.; Pena, M. Formation of urea dipeptides from carbonyldiimidazole: Application toward the protease inhibitors GE20372 and MAPI. J. Org. Chem. 1997, 62, 6420-6423;
    • (1997) J. Org. Chem. , vol.62 , pp. 6420-6423
    • Zhang, X.1    Rodrigues, J.2    Evans, L.3    Hinckle, B.4    Ballantyne, L.5    Pena, M.6
  • 23
    • 0001225507 scopus 로고    scopus 로고
    • A general synthesis of unsymmetrical tetrasubstituted ureas
    • (f) Katritzky, A. R.; Pleynet, D. P. M.; Yang, B. A general synthesis of unsymmetrical tetrasubstituted ureas. J. Org. Chem. 1997, 62, 4155-4158.
    • (1997) J. Org. Chem. , vol.62 , pp. 4155-4158
    • Katritzky, A.R.1    Pleynet, D.P.M.2    Yang, B.3
  • 24
    • 33751391068 scopus 로고
    • An improved method for the synthesis of enantiomerically pure amino acid ester isocyanates
    • (a) Nowick, J. S.; Powell, N. A.; Nguyen, T. M.; Noronha, G. An improved method for the synthesis of enantiomerically pure amino acid ester isocyanates. J. Org. Chem. 1992, 57, 7364-7366;
    • (1992) J. Org. Chem. , vol.57 , pp. 7364-7366
    • Nowick, J.S.1    Powell, N.A.2    Nguyen, T.M.3    Noronha, G.4
  • 25
    • 0033550306 scopus 로고    scopus 로고
    • Effective preparation of O-succinimidyl-2-(tert-butoxycarbonylamino) ethylcarbamate derivatives from β-amino acids application to the synthesis of urea-containing pseudopeptides and oligoureas
    • (b) Guichard, G.; Semetey, V.; Didierjean, C.; Aubry, A.; Briand, J.-P.; Rodriguez, M. Effective preparation of O-succinimidyl-2-(tert- butoxycarbonylamino)ethylcarbamate derivatives from β-amino acids Application to the synthesis of urea-containing pseudopeptides and oligoureas. J. Org. Chem. 1999, 64, 8702-8705;
    • (1999) J. Org. Chem. , vol.64 , pp. 8702-8705
    • Guichard, G.1    Semetey, V.2    Didierjean, C.3    Aubry, A.4    Briand, J.-P.5    Rodriguez, M.6
  • 26
    • 0040183791 scopus 로고    scopus 로고
    • Selected synthesis of ureas through phosgene substitutes
    • (c) Bigi, F.; Maggi, R.; Sartori, G. Selected synthesis of ureas through phosgene substitutes. Green Chem. 2000, 2, 140-148.
    • (2000) Green Chem. , vol.2 , pp. 140-148
    • Bigi, F.1    Maggi, R.2    Sartori, G.3
  • 27
    • 0141817222 scopus 로고
    • Formation and properties of some uretediones
    • Raiford, L. C.; Freyermuth, H. B. Formation and properties of some uretediones. J. Org. Chem. 1943, 8, 230-238.
    • (1943) J. Org. Chem. , vol.8 , pp. 230-238
    • Raiford, L.C.1    Freyermuth, H.B.2
  • 28
    • 21044444983 scopus 로고    scopus 로고
    • Process for preparing 1,3-disubstituted urea. US Patent No. 5,902,899, May 11, 1999
    • Hayashi, T.; Yasuoka, J. Process for preparing 1,3-disubstituted urea. US Patent No. 5,902,899, May 11, 1999.
    • Hayashi, T.1    Yasuoka, J.2
  • 29
    • 0001337796 scopus 로고
    • Oxidative coupling of amines and carbon monoxide catalyzed by palladium complexes. Mono- and double carbonylation reactions promoted by iodine compounds
    • Pri-Bar, I.; Alper, H. Oxidative coupling of amines and carbon monoxide catalyzed by palladium complexes. Mono- and double carbonylation reactions promoted by iodine compounds. Can. J. Chem.-Rev. Can. Chim. 1990, 68, 1544-1547.
    • (1990) Can. J. Chem.-Rev. Can. Chim. , vol.68 , pp. 1544-1547
    • Pri-Bar, I.1    Alper, H.2
  • 30
    • 0027558559 scopus 로고
    • Novel palladium (II)-catalyzed direct synthesis of polymers with oxamide and urea linkages
    • Dahlen, G. M.; Sen, A. Novel palladium (II)-catalyzed direct synthesis of polymers with oxamide and urea linkages. Macromolecules 1993, 26, 1784-1786.
    • (1993) Macromolecules , vol.26 , pp. 1784-1786
    • Dahlen, G.M.1    Sen, A.2
  • 31
    • 0030762977 scopus 로고    scopus 로고
    • Activity of homogeneous transition metal catalysts for oxidative carbonylation of aniline to N, N′-diphenyl urea
    • Gupte, S. P.; Rode, C. V.; Kelkar, A. A.; Mulla, S. A. R. Activity of homogeneous transition metal catalysts for oxidative carbonylation of aniline to N, N′-diphenyl urea. J. Mol. Catal. A: Chem. 1997, 122, 103-109.
    • (1997) J. Mol. Catal. A: Chem. , vol.122 , pp. 103-109
    • Gupte, S.P.1    Rode, C.V.2    Kelkar, A.A.3    Mulla, S.A.R.4
  • 32
    • 0025434282 scopus 로고
    • Acyclic and cyclic urea formation via the cobalt-catalyzed oxidative carbonylation of aromatic primary amines
    • Bassoli, A.; Rindone, B.; Tollari, S.; Chioccara, F. Acyclic and cyclic urea formation via the cobalt-catalyzed oxidative carbonylation of aromatic primary amines. J. Mol. Catal. 1990, 60, 41-48.
    • (1990) J. Mol. Catal. , vol.60 , pp. 41-48
    • Bassoli, A.1    Rindone, B.2    Tollari, S.3    Chioccara, F.4
  • 33
    • 0000807051 scopus 로고
    • A mechanistic investigation of the decarbonyldimanganese-catalyzed carbonylation of amines
    • Dombek, B. D.; Angelici, R. J. A mechanistic investigation of the decarbonyldimanganese-catalyzed carbonylation of amines. J. Organomet. Chem. 1977, 134, 203-217.
    • (1977) J. Organomet. Chem. , vol.134 , pp. 203-217
    • Dombek, B.D.1    Angelici, R.J.2
  • 34
    • 0000580772 scopus 로고
    • A new synthesis of ureas. The reaction of ammonia or aliphatic amines with carbon monoxide in the presence of selenium
    • Sonoda, N.; Yasuhara, T.; Kondo, K.; Ikeda, T.; Tsutsumi, S. A new synthesis of ureas. The reaction of ammonia or aliphatic amines with carbon monoxide in the presence of selenium. J. Am. Chem. Soc. 1971, 93, 6344.
    • (1971) J. Am. Chem. Soc. , vol.93 , pp. 6344
    • Sonoda, N.1    Yasuhara, T.2    Kondo, K.3    Ikeda, T.4    Tsutsumi, S.5
  • 35
    • 0001281977 scopus 로고
    • Selenium-assisted carbonylation with carbon monooxide
    • Sonoda, N. Selenium-assisted carbonylation with carbon monooxide. Pure Appl. Chem. 1993, 65, 699-707.
    • (1993) Pure Appl. Chem. , vol.65 , pp. 699-707
    • Sonoda, N.1
  • 36
    • 0034714527 scopus 로고    scopus 로고
    • 6-catalyzed oxidative carbonylation of primary amines to N, N′-disubstituted ureas in single or biphasic solvent system. Optimization and functional group compatibility studies
    • 6-catalyzed oxidative carbonylation of primary amines to N, N′-disubstituted ureas in single or biphasic solvent system. Optimization and functional group compatibility studies. J. Org. Chem. 2000, 65, 5216-5222.
    • (2000) J. Org. Chem. , vol.65 , pp. 5216-5222
    • McCusker, J.E.1    Main, A.D.2    Johnson, K.S.3    Grasso, C.A.4    McElwee-White, L.5
  • 37
    • 0034703265 scopus 로고    scopus 로고
    • Catalytic oxidative carbonylation of aliphatic secondary amines to tetra substituted ureas
    • McCusker, J. E.; Qian, F.; McElwee-White, L. Catalytic oxidative carbonylation of aliphatic secondary amines to tetra substituted ureas. J. Mol. Catal. A: Chem. 2000, 159, 11-17.
    • (2000) J. Mol. Catal. A: Chem. , vol.159 , pp. 11-17
    • McCusker, J.E.1    Qian, F.2    McElwee-White, L.3
  • 38
    • 0035843402 scopus 로고    scopus 로고
    • -2 supported palladium catalyst for syntheses of disubstituted ureas from amines by oxidative carbonylation
    • -2 supported palladium catalyst for syntheses of disubstituted ureas from amines by oxidative carbonylation. Tetrahedron Lett. 2001, 42, 2161-2163.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 2161-2163
    • Shi, F.1    Deng, Y.2    Sima, T.3    Yang, H.4
  • 39
    • 0035911001 scopus 로고    scopus 로고
    • A simple conversion of amines into mono substituted ureas in organic and aqueous solvents
    • Liu, Q.; Luedtke, N. W.; Yitzhak, T. A simple conversion of amines into mono substituted ureas in organic and aqueous solvents. Tetrahedron Lett. 2001, 42, 1445-1447.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 1445-1447
    • Liu, Q.1    Luedtke, N.W.2    Yitzhak, T.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.