Environmentally Benign One-Pot Synthesis of Cyanamides from Dithiocarbamates Using I₂ and H₂O₂

REFERENCES

• Brown , M. D. ; Gillon , D. W. ; Meakins , G. D. ; Whitham , G. H. A new general synthesis of N-mono- and N-disubstituted 2-aminothiazoles . J. Chem. Soc. Chem. Commun. 1982 , 444 – 445 .
   Google Scholar
• (a) Gilman , A. G. ; Goodman , L. S. ; Rall , T. W. ; Murad , F. Goodman and Gilman's the Pharmacological Basis of Therapeutics ; Pergamon Press : New York , 1990 ; (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 .
   Google Scholar
• 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 .
   PubMed Web of Science ®Google Scholar
• Novelli , A. Hydantoins of β-tetralone. Anales Farm. y Bioquim. 1954, 21, 81–84.
   Google Scholar
• (a) McCall , J. M. ; Tenbrink , R. E. ; Ursprung , J. J. A new approach to triaminopyrimidine n-oxides . J. Org. Chem. 1975 , 40 , 3304 – 3306 ; (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 ; (c) Robinson , J. R. ; Brown , W. H. Diphenylcyanamide derivatives . Can. J. Chem. 1951 , 29 , 1069 – 1074 .
   PubMed Web of Science ®Google Scholar
• Stephens , R. W. ; Domeier , L. A. ; Todd , M. G. ; Nelson , V. A. N-Cyanoimides: Reactivity studies with amine nucleophiles . Tetrahedron Lett. 1992 , 33 , 733 – 736 .
   Web of Science ®Google Scholar
• (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 ; (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 ; (c) Currie , A. C. ; Newbold , G. T. ; Spring , F. S. 14-Hydroxynorcodeine and its derivatives . J. Chem. Soc. 1961 , 4693 – 4700 .
   Google Scholar
• Hulme , R. ; Zamora , O. D. P. ; Mota , E. J. ; Pastén , M. A. ; Contreras-Rojas , R. ; Miranda , R. ; Valencia-Hernández , I. ; Correa-Basurto , J. ; Trujillo-Ferrara , J. ; Delgado , F. Cyanamide: A convenient building block to synthesize 4-aryl-2-cyanoimino-3,4-dihydro-1H-pyrimidine systems via a multicomponent reaction . Tetrahedron 2008 , 64 , 3372 – 3380 .
   Web of Science ®Google Scholar
• (a) Yagupolskii , L. M. ; Antepohl , W. ; Artunc , F. ; Handrock , R. ; Klebanov , B. M. ; Maletina , I. I. ; Marxen , B. ; Petko , K. I. ; Quast , U. ; Vogt , A. ; Weiss , C. ; Zibold , J. ; Herzig , S. Vasorelaxation by new hybrid compounds containing dihydropyridine and pinacidil-like moieties . J. Med. Chem. 1999 , 42 , 5266 – 5271 ; (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 .
   PubMed Web of Science ®Google Scholar
• Kreutzberger , A. ; Sellheim , M. Antimycotics XIX: 4,6-Disubstituted 2-(cyanamino) pyrimidines . J. Heterocycl. Chem. 1985 , 22 , 721 – 723 .
   Web of Science ®Google Scholar
• (a) Von Braun , J. Action of cyanogen bromide on tertiary amines . Ber. Dtsch. Chem. Ges. 1900 , 33 , 1438 – 1452 ; (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 ; (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 .
   Google Scholar
• Wheland , R. C. ; Martin , E. L. Synthesis of substituted 7,7,8,8-tetracyanoquinodimethanes . J. Org. Chem. 1975 , 40 , 3101 – 3109 .
   Web of Science ®Google Scholar
• Davis , W. A. ; Cava , M. P. A new synthesis of arylmalononitriles . J. Org. Chem. 1983 , 48 , 2774 – 2775 .
   Web of Science ®Google Scholar
• (a) Van Leusen , A. M. ; Jagt , J. C. Chemistry of sulfonyl cyanides, II: Nucleophilic displacements on sulfonyl cyanides . Tetrahedron Lett. 1970 , 12 , 967 – 970 ; (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 .
   Google Scholar
• 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 .
   PubMed Web of Science ®Google Scholar
• Kim , J.-J. ; Kweon , D.-H. ; Cho , S.-D. ; Kim , H.-K. ; Jung , E.-Y. ; Lee , S.-G. ; Falckd , J. R. ; Yoona , Y.-J. 2-Cyanopyridazin-3(2H)-ones: Effective and chemoselective electrophilic cyanating agents . Tetrahedron 2005 , 61 , 5889 – 5894 .
   Web of Science ®Google Scholar
• (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; (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.
   Web of Science ®Google Scholar
• 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 .
   PubMed Web of Science ®Google Scholar
• (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 ; (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 ; (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 .
   PubMed Web of Science ®Google Scholar
• 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 .
   Web of Science ®Google Scholar
• Bahrami , K. ; Khodaei , M. M. ; Tirandaz , Y. Desulfurization of thioamides into amides with H2O2/ZrCl4 reagent system . Synthesis 2009 , 369 – 371 .
   Web of Science ®Google Scholar
• Grellepois , F. ; Portella , C. Facile conversion of dithioesters into carboxylic acids or esters using alkaline hydrogen peroxide . Synthesis 2008 , 3443 – 3446 .
   Web of Science ®Google Scholar
• Grivas , S. ; Ronne , E. ; Olsson , K. Facile desulfurization of cyclic thioureas by hydrogen peroxide in acetic acid . Acta Chem. Scand. 1995 , 49 , 225 – 229 .
   PubMedGoogle Scholar
• 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 .
   Web of Science ®Google Scholar
• 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 .
   PubMed Web of Science ®Google Scholar