메뉴 건너뛰기




Volumn 42, Issue 7, 2012, Pages 951-958

Environmentally benign one-pot synthesis of cyanamides from dithiocarbamates using I 2 and H 2O 2

Author keywords

Cyanamide; Dithiocarbamate salt; Hydrogen peroxide; Iodine; Isothiocyanate

Indexed keywords

ACETIC ACID ETHYL ESTER; AMMONIA; BICARBONATE; CYANAMIDE; DITHIOCARBAMIC ACID; DITHIOCARBAMIC ACID DERIVATIVE; HYDROGEN PEROXIDE; IODINE; ISOTHIOCYANIC ACID; PHENYLTHIOUREA; SULFUR; WATER;

EID: 84055223410     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2010.532276     Document Type: Article
Times cited : (33)

References (37)
  • 3
    • 0014256740 scopus 로고
    • The Correlation between the antitumor activities and chemical structures of thiocyanato derivatives of purines and their Ribonucleosides
    • (b) Saneyoshi, M.; Tokuzen, R.; Maeda, M.; Fukuoka, F. The Correlation between the antitumor activities and chemical structures of thiocyanato derivatives of purines and their Ribonucleosides. Chem. Pharm. Bull. 1968, 16, 505-508.
    • (1968) Chem. Pharm. Bull. , vol.16 , pp. 505-508
    • Saneyoshi, M.1    Tokuzen, R.2    Maeda, M.3    Fukuoka, F.4
  • 4
    • 0026687040 scopus 로고
    • Synthesis and antiarrhythmic activity of 2,2-dialkyl-1′-(N- substituted aminoalkyl)-spiro-(chroman-4,4′-imidazolidine)-2′, 5′-diones
    • Matsukura, M.; Daiku, Y.; Ueda, K.; Tanaka, S.; Igarashi, T.; Minami, N. Synthesis and antiarrhythmic activity of 2,2-dialkyl-1′-(N-substituted aminoalkyl)-spiro-(chroman-4,4′-imidazolidine)-2′,5′-diones. Chem. Pharm. Bull. 1992, 40, 1823-1827.
    • (1992) Chem. Pharm. Bull. , vol.40 , pp. 1823-1827
    • Matsukura, M.1    Daiku, Y.2    Ueda, K.3    Tanaka, S.4    Igarashi, T.5    Minami, N.6
  • 5
    • 0002275733 scopus 로고
    • Hydantoins of β-tetralone
    • Novelli, A. Hydantoins of β-tetralone. Anales Farm. y Bioquim. 1954, 21, 81-84.
    • (1954) Anales Farm. y Bioquim. , vol.21 , pp. 81-84
    • Novelli, A.1
  • 6
    • 0016866197 scopus 로고
    • A new approach to triaminopyrimidine n-oxides
    • (a) McCall, J. M.; Tenbrink, R. E.; Ursprung, J. J. A new approach to triaminopyrimidine n-oxides. J. Org. Chem. 1975, 40, 3304-3306;
    • (1975) J. Org. Chem. , vol.40 , pp. 3304-3306
    • McCall, J.M.1    Tenbrink, R.E.2    Ursprung, J.J.3
  • 7
    • 6844257516 scopus 로고    scopus 로고
    • Synthesis and pharmacological evaluation of N-(2,5-disubstituted phenyl)-N′-(3-substituted phenyl)-N′-methylguanidines as N-methyl-D-aspartate receptor ion-channel blockers
    • (b) Hu, L. Y.; Guo, J.; Magar, S.; Fischer, J. B.; Burke-Howie, K. J.; Durant, G. J. Synthesis and pharmacological evaluation of N-(2,5-disubstituted phenyl)-N′-(3-substituted phenyl)-N′-methylguanidines as N-methyl-D-aspartate receptor ion-channel blockers. J. Med. Chem. 1997, 40, 4281-4289;
    • (1997) J. Med. Chem. , vol.40 , pp. 4281-4289
    • Hu, L.Y.1    Guo, J.2    Magar, S.3    Fischer, J.B.4    Burke-Howie, K.J.5    Durant, G.J.6
  • 8
    • 3743079439 scopus 로고
    • Diphenylcyanamide derivatives
    • (c) Robinson, J. R.; Brown, W. H. Diphenylcyanamide derivatives. Can. J. Chem. 1951, 29, 1069-1074.
    • (1951) Can. J. Chem. , vol.29 , pp. 1069-1074
    • Robinson, J.R.1    Brown, W.H.2
  • 10
    • 0141430544 scopus 로고
    • Secondary amines from cyanamides: A new method for removing the cyano group
    • (a) Donetti, A.; Omodei-Sale, A.; Mantegani A.; Zugna, E. Secondary amines from cyanamides: A new method for removing the cyano group. Tetrahedron Lett. 1969, 39, 3327-3328;
    • (1969) Tetrahedron Lett. , vol.39 , pp. 3327-3328
    • Donetti, A.1    Omodei-Sale, A.2    Mantegani, A.3    Zugna, E.4
  • 11
    • 0141653466 scopus 로고
    • New heterocyclic systems I: 5,6-Dihydro-7H, 12H-dibenz [c,f] azocine
    • (b) Pala, G.; Mantegani, A.; Zugna, E. New heterocyclic systems I: 5,6-Dihydro-7H, 12H-dibenz [c,f] azocine. Tetrahedron 1970, 26, 1275-1279;
    • (1970) Tetrahedron , vol.26 , pp. 1275-1279
    • Pala, G.1    Mantegani, A.2    Zugna, E.3
  • 15
    • 0029559349 scopus 로고
    • Pinacidil relaxes porcine and human coronary arteries by activating ATP-dependent potassium channels in smooth muscle cells
    • (b) Gollasch, M.; Bychkov, R.; Ried, C.; Behrendt, F.; Scholze, S.; Luft, F. C.; Haller, H. Pinacidil relaxes porcine and human coronary arteries by activating ATP-dependent potassium channels in smooth muscle cells. J. Pharmacol. Exp. Ther. 1995, 275, 681-692.
    • (1995) J. Pharmacol. Exp. Ther. , vol.275 , pp. 681-692
    • Gollasch, M.1    Bychkov, R.2    Ried, C.3    Behrendt, F.4    Scholze, S.5    Luft, F.C.6    Haller, H.7
  • 16
    • 0022178434 scopus 로고
    • Antimycotics XIX: 4,6-Disubstituted 2-(cyanamino) pyrimidines
    • Kreutzberger, A.; Sellheim, M. Antimycotics XIX: 4,6-Disubstituted 2-(cyanamino) pyrimidines. J. Heterocycl. Chem. 1985, 22, 721-723.
    • (1985) J. Heterocycl. Chem. , vol.22 , pp. 721-723
    • Kreutzberger, A.1    Sellheim, M.2
  • 17
    • 84914602862 scopus 로고
    • Action of cyanogen bromide on tertiary amines
    • (a) Von Braun, J. Action of cyanogen bromide on tertiary amines. Ber. Dtsch. Chem. Ges. 1900, 33, 1438-1452;
    • (1900) Ber. Dtsch. Chem. Ges. , vol.33 , pp. 1438-1452
    • Von Braun, J.1
  • 18
    • 6844257516 scopus 로고    scopus 로고
    • Synthesis and pharmacological evaluation of N-(2,5-disubstituted phenyl)-N′-(3-substituted phenyl)-N′-methylguanidines as N-methyl-D-aspartate receptor ion-channel blockers
    • (b) Hu, L. Y.; Guo, J.; Magar, S. S.; Fischer, J. B.; Burke-Howie, K. J.; Durant, G. J. Synthesis and pharmacological evaluation of N-(2,5-disubstituted phenyl)-N′-(3-substituted phenyl)-N′-methylguanidines as N-methyl-D-aspartate receptor ion-channel blockers. J. Med. Chem. 1997, 40, 4281-4289;
    • (1997) J. Med. Chem. , vol.40 , pp. 4281-4289
    • Hu, L.Y.1    Guo, J.2    Magar, S.S.3    Fischer, J.B.4    Burke-Howie, K.J.5    Durant, G.J.6
  • 19
    • 0031774549 scopus 로고    scopus 로고
    • Quantitative gas-solid reactions with ClCN and BrCN: Synthesis of cyanamides, cyanates, thiocyanates, and their derivatives
    • (c) Kaupp, G.; Schmeyers, J.; Boy, J. Quantitative gas-solid reactions with ClCN and BrCN: Synthesis of cyanamides, cyanates, thiocyanates, and their derivatives. Chem. Eur. J. 1998, 4, 2467-2474.
    • (1998) Chem. Eur. J. , vol.4 , pp. 2467-2474
    • Kaupp, G.1    Schmeyers, J.2    Boy, J.3
  • 20
    • 33847801064 scopus 로고
    • Synthesis of substituted 7,7,8,8-tetracyanoquinodimethanes
    • Wheland, R. C.; Martin, E. L. Synthesis of substituted 7,7,8,8-tetracyanoquinodimethanes. J. Org. Chem. 1975, 40, 3101-3109.
    • (1975) J. Org. Chem. , vol.40 , pp. 3101-3109
    • Wheland, R.C.1    Martin, E.L.2
  • 21
    • 0000942557 scopus 로고
    • A new synthesis of arylmalononitriles
    • Davis, W. A.; Cava, M. P. A new synthesis of arylmalononitriles. J. Org. Chem. 1983, 48, 2774-2775.
    • (1983) J. Org. Chem. , vol.48 , pp. 2774-2775
    • Davis, W.A.1    Cava, M.P.2
  • 22
    • 0011098403 scopus 로고
    • Chemistry of sulfonyl cyanides, II: Nucleophilic displacements on sulfonyl cyanides
    • (a) Van Leusen, A. M.; Jagt, J. C. Chemistry of sulfonyl cyanides, II: Nucleophilic displacements on sulfonyl cyanides. Tetrahedron Lett. 1970, 12, 967-970;
    • (1970) Tetrahedron Lett. , vol.12 , pp. 967-970
    • Van Leusen, A.M.1    Jagt, J.C.2
  • 23
    • 0000772914 scopus 로고    scopus 로고
    • A convenient new synthesis of 1-cyanobenzotriazole and its use as a C-cyanating reagent
    • (b) Hughes, T. V.; Hammond, S. D.; Cava, M. P. A convenient new synthesis of 1-cyanobenzotriazole and its use as a C-cyanating reagent. J. Org. Chem. 1998, 63, 401-402.
    • (1998) J. Org. Chem. , vol.63 , pp. 401-402
    • Hughes, T.V.1    Hammond, S.D.2    Cava, M.P.3
  • 24
    • 0000487930 scopus 로고    scopus 로고
    • 1-Cyanoimidazole as a mild and efficient electrophilic cyanating agent
    • Wu, Y.-Q.; Limburg, D. C.; Wilkinson, D. E.; Hamilton, G. S. 1-Cyanoimidazole as a mild and efficient electrophilic cyanating agent. Org. Lett. 2000, 2, 795-797.
    • (2000) Org. Lett. , vol.2 , pp. 795-797
    • Wu, Y.-Q.1    Limburg, D.C.2    Wilkinson, D.E.3    Hamilton, G.S.4
  • 26
    • 33644994791 scopus 로고    scopus 로고
    • Sodium bis(trimethylsilyl)amide in the "one-flask," transformation of isocyanates to cyanamides
    • (a) Wong, F. F.; Chen, C.-Y.; Yeh, M.-Y. Sodium bis(trimethylsilyl)amide in the "one-flask" transformation of isocyanates to cyanamides. Synlett. 2006, 559-562;
    • (2006) Synlett. , pp. 559-562
    • Wong, F.F.1    Chen, C.-Y.2    Yeh, M.-Y.3
  • 27
    • 53149139686 scopus 로고    scopus 로고
    • Desulfurization and transformation of isothiocyanates to cyanamides by using sodium bis(trimethylsilyl) amide
    • (b) Chen, C.-Y.; Wong, F. F.; Huang, J.-J.; Lin, S.-K.; Yeh, M.-Y. Desulfurization and transformation of isothiocyanates to cyanamides by using sodium bis(trimethylsilyl) amide. Tetrahedron Lett. 2008, 49, 6505-6507.
    • (2008) Tetrahedron Lett. , vol.49 , pp. 6505-6507
    • Chen, C.-Y.1    Wong, F.F.2    Huang, J.-J.3    Lin, S.-K.4    Yeh, M.-Y.5
  • 28
    • 0036263378 scopus 로고    scopus 로고
    • Cyanamide synthesis by the palladium-catalyzed cleavage of a Si-N bond
    • Kamijo, S.; Jin, T.; Yamamoto, Y. Cyanamide synthesis by the palladium-catalyzed cleavage of a Si-N bond. Angew. Chem. Int. Ed. 2002, 41, 1780-1782.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 1780-1782
    • Kamijo, S.1    Jin, T.2    Yamamoto, Y.3
  • 29
    • 41649119009 scopus 로고    scopus 로고
    • Hypervalent iodine(III)-mediated regioselective N-acylation of 1,3-disubstituted thioureas
    • (a) Singh, C. B.; Ghosh, H.; Murru, S.; Patel, B. K. Hypervalent iodine(III)-mediated regioselective N-acylation of 1,3-disubstituted thioureas. J. Org. Chem. 2008, 73, 2924-2927;
    • (2008) J. Org. Chem. , vol.73 , pp. 2924-2927
    • Singh, C.B.1    Ghosh, H.2    Murru, S.3    Patel, B.K.4
  • 30
    • 57349191553 scopus 로고    scopus 로고
    • Desulfurization mediated by hypervalent iodine(III): A novel strategy for the construction of heterocycles
    • (b) Ghosh, H.; Yella, R.; Nath, J.; Patel, B. K. Desulfurization mediated by hypervalent iodine(III): A novel strategy for the construction of heterocycles. Eur. J. Org. Chem. 2008, 6189-6196;
    • (2008) Eur. J. Org. Chem. , pp. 6189-6196
    • Ghosh, H.1    Yella, R.2    Nath, J.3    Patel, B.K.4
  • 31
    • 63649122966 scopus 로고    scopus 로고
    • An efficient synthesis of cyanamide from amine promoted by a hypervalent iodine(III) reagent
    • (c) Ghosh, H.; Yella, R.; Ali, A. R.; Sahoo, S. K.; Patel, B. K. An efficient synthesis of cyanamide from amine promoted by a hypervalent iodine(III) reagent. Tetrahedron Lett. 2009, 50, 2407-2410.
    • (2009) Tetrahedron Lett. , vol.50 , pp. 2407-2410
    • Ghosh, H.1    Yella, R.2    Ali, A.R.3    Sahoo, S.K.4    Patel, B.K.5
  • 32
    • 70350052996 scopus 로고    scopus 로고
    • A one-pot preparation of cyanamide from dithiocarbamate using molecular iodine
    • Nath, J.; Patel, B. K.; Jamir, L.; Sinha, U. B.; Satyanarayana, K. V. V. V. A one-pot preparation of cyanamide from dithiocarbamate using molecular iodine. Green Chem. 2009, 11, 1503-1506.
    • (2009) Green Chem. , vol.11 , pp. 1503-1506
    • Nath, J.1    Patel, B.K.2    Jamir, L.3    Sinha, U.B.4    Satyanarayana, K.V.V.V.5
  • 34
    • 56249117676 scopus 로고    scopus 로고
    • Facile conversion of dithioesters into carboxylic acids or esters using alkaline hydrogen peroxide
    • Grellepois, F.; Portella, C. Facile conversion of dithioesters into carboxylic acids or esters using alkaline hydrogen peroxide. Synthesis 2008, 3443-3446.
    • (2008) Synthesis , pp. 3443-3446
    • Grellepois, F.1    Portella, C.2
  • 35
    • 0029266170 scopus 로고
    • Facile desulfurization of cyclic thioureas by hydrogen peroxide in acetic acid
    • Grivas, S.; Ronne, E.; Olsson, K. Facile desulfurization of cyclic thioureas by hydrogen peroxide in acetic acid. Acta Chem. Scand. 1995, 49, 225-229.
    • (1995) Acta Chem. Scand. , vol.49 , pp. 225-229
    • Grivas, S.1    Ronne, E.2    Olsson, K.3
  • 36
    • 0027981411 scopus 로고
    • Oxidation of thiourethanes, XII: Oxidative desulfuration of cyclic dithiocarbamates and carbazates using hydrogenperoxide or hydrogenperoxide/ sodium tungstate in a two-phase-system
    • Hanefeld, W.; Schlitzer, M. Oxidation of thiourethanes, XII: Oxidative desulfuration of cyclic dithiocarbamates and carbazates using hydrogenperoxide or hydrogenperoxide/sodium tungstate in a two-phase-system. Arch. Pharm. 1994, 327, 413-415.
    • (1994) Arch. Pharm. , vol.327 , pp. 413-415
    • Hanefeld, W.1    Schlitzer, M.2
  • 37
    • 0000795701 scopus 로고    scopus 로고
    • An improved procedure for the preparation of isothiocyanates from primary amines by using hydrogen peroxide as the dehydrosulfurization reagent
    • Li, G.; Tajima, H.; Ohtani, T. An improved procedure for the preparation of isothiocyanates from primary amines by using hydrogen peroxide as the dehydrosulfurization reagent. J. Org. Chem. 1997, 62, 4539-4540.
    • (1997) J. Org. Chem. , vol.62 , pp. 4539-4540
    • Li, G.1    Tajima, H.2    Ohtani, T.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.