메뉴 건너뛰기




Volumn 1, Issue 10, 2013, Pages 1319-1325

Chemical behavior and reaction kinetics of sulfur and nitrogen half-mustard and iprit carbonate analogues

Author keywords

Anchimeric effect; Dimethyl carbonate; Green chemistry; Kinetics; Mustard compound

Indexed keywords

ANCHIMERIC EFFECT; CHEMICAL BEHAVIOR; DIMETHYL CARBONATE; GREEN CHEMISTRY; MUSTARD COMPOUND; NITROGEN MUSTARDS; ORGANIC MOLECULES;

EID: 84885338299     PISSN: None     EISSN: 21680485     Source Type: Journal    
DOI: 10.1021/sc4001737     Document Type: Article
Times cited : (16)

References (47)
  • 2
    • 0029931420 scopus 로고    scopus 로고
    • Toxicology and pharmacology of the chemical warfare agent sulfur mustard
    • Dacre, J. C.; Goldman, M. Toxicology and pharmacology of the chemical warfare agent sulfur mustard Pharmacol. Rev. 1996, 48, 289-326
    • (1996) Pharmacol. Rev. , vol.48 , pp. 289-326
    • Dacre, J.C.1    Goldman, M.2
  • 3
    • 77949418282 scopus 로고    scopus 로고
    • Detoxication of sulfur half-mustards by nucleophilic scavengers: Robust activity of thiopurines
    • Liu, J.; Powell, K. L.; Thames, H. D.; MacLeod, M. C. Detoxication of sulfur half-mustards by nucleophilic scavengers: robust activity of thiopurines Chem. Res. Toxicol. 2010, 23, 488-496
    • (2010) Chem. Res. Toxicol. , vol.23 , pp. 488-496
    • Liu, J.1    Powell, K.L.2    Thames, H.D.3    MacLeod, M.C.4
  • 4
    • 84862907701 scopus 로고    scopus 로고
    • Molecular thioamide â†" iminothiolate switches for sulfur mustards
    • Wang, Q.-Q.; Begum, R. A.; Day, V. W.; Bowman-James, K. Molecular thioamide â†" iminothiolate switches for sulfur mustards Inorg. Chem. 2012, 51, 760-762
    • (2012) Inorg. Chem. , vol.51 , pp. 760-762
    • Wang, Q.-Q.1    Begum, R.A.2    Day, V.W.3    Bowman-James, K.4
  • 5
    • 79551678796 scopus 로고    scopus 로고
    • A model of the [FeFe] hydrogenase active site with a biologically relevant azadithiolate bridge: A spectroscopic and theoretical investigation
    • Erdem, O. F.; Silakov, A.; Reijerse, E.; Lubitz, W.; Lennart, K.-G. S.; Huang, P.; Ott, S.; Stein, M. A model of the [FeFe] hydrogenase active site with a biologically relevant azadithiolate bridge: A spectroscopic and theoretical investigation Angew. Chem., Int. Ed. 2011, 50, 1439-1443
    • (2011) Angew. Chem., Int. Ed. , vol.50 , pp. 1439-1443
    • Erdem, O.F.1    Silakov, A.2    Reijerse, E.3    Lubitz, W.4    Lennart, K.-G.S.5    Huang, P.6    Ott, S.7    Stein, M.8
  • 6
    • 77956455543 scopus 로고    scopus 로고
    • Synthesis of N,N′-bis(thioether)-functionalized imidazolium salts: Their reactivity towards Ag and Pd complexes and first S,CNHC,S free carbene
    • Fliedel, C.; Sabbatini, A.; Braunstein, P. Synthesis of N,N′-bis(thioether)-functionalized imidazolium salts: their reactivity towards Ag and Pd complexes and first S,CNHC,S free carbene Dalton Trans. 2010, 39, 8820-8828
    • (2010) Dalton Trans. , vol.39 , pp. 8820-8828
    • Fliedel, C.1    Sabbatini, A.2    Braunstein, P.3
  • 8
    • 84055190948 scopus 로고    scopus 로고
    • Synthesis of an azide-bearing N-mustard analogue of S-adenosyl-L- methionine
    • Mai, V.; Comstock, L. R. Synthesis of an azide-bearing N-mustard analogue of S-adenosyl-L-methionine J. Org. Chem. 2011, 76, 10319-10324
    • (2011) J. Org. Chem. , vol.76 , pp. 10319-10324
    • Mai, V.1    Comstock, L.R.2
  • 9
    • 84858974978 scopus 로고    scopus 로고
    • Practical method for parallel synthesis of diversely substituted 1-phenylpiperazines
    • Konstantinova, I.; Bukhryakov, K.; Gezentsvey, Y.; Krasavin, M. Practical method for parallel synthesis of diversely substituted 1-phenylpiperazines Lett. Org. Chem. 2011, 8, 628-630
    • (2011) Lett. Org. Chem. , vol.8 , pp. 628-630
    • Konstantinova, I.1    Bukhryakov, K.2    Gezentsvey, Y.3    Krasavin, M.4
  • 10
    • 78650853294 scopus 로고    scopus 로고
    • Palladium-catalyzed direct and regioselective C-H bond functionalization/oxidative acetoxylation of indoles
    • Choy, R. P. Y.; Lau, C. P.; Kwong, F. Y. Palladium-catalyzed direct and regioselective C-H bond functionalization/oxidative acetoxylation of indoles J. Org. Chem. 2011, 76, 80-84
    • (2011) J. Org. Chem. , vol.76 , pp. 80-84
    • Choy, R.P.Y.1    Lau, C.P.2    Kwong, F.Y.3
  • 11
    • 0038049527 scopus 로고    scopus 로고
    • Triflic anhydride-promoted cyclization of sulfides: A convenient synthesis of fused sulfur heterocycles
    • Shevchenko, N. E.; Nenajdenko, V. G.; Balenkova, E. S. Triflic anhydride-promoted cyclization of sulfides: A convenient synthesis of fused sulfur heterocycles Synthesis 2003, 8, 1191-1200
    • (2003) Synthesis , vol.8 , pp. 1191-1200
    • Shevchenko, N.E.1    Nenajdenko, V.G.2    Balenkova, E.S.3
  • 12
    • 0034731550 scopus 로고    scopus 로고
    • Photochemistry of MTM- and MTE-esters of ω-phthalimido carboxylic acids: Macrocyclization versus deprotection
    • Griesbeck, A. G.; Oelgemoeller, M.; Lex, J. Photochemistry of MTM- and MTE-esters of ω-phthalimido carboxylic acids: Macrocyclization versus deprotection J. Org. Chem. 2000, 65, 9028-9032
    • (2000) J. Org. Chem. , vol.65 , pp. 9028-9032
    • Griesbeck, A.G.1    Oelgemoeller, M.2    Lex, J.3
  • 13
    • 79851475192 scopus 로고    scopus 로고
    • Conjugated zwitterionic polyelectrolyte as the charge injection layer for high-performance polymer light-emitting diodes
    • Fang, J.; Wallikewitz, B. H.; Gao, F.; Tu, G.; Muller, C.; Pace, G.; Friend, R. H.; Huck, T. S. Conjugated zwitterionic polyelectrolyte as the charge injection layer for high-performance polymer light-emitting diodes J. Am. Chem. Soc. 2011, 133, 683-685
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 683-685
    • Fang, J.1    Wallikewitz, B.H.2    Gao, F.3    Tu, G.4    Muller, C.5    Pace, G.6    Friend, R.H.7    Huck, T.S.8
  • 14
    • 79953219471 scopus 로고    scopus 로고
    • Promoting the formation and stabilization of human telomeric G-quadruplex DNA, inhibition of telomerase and cytotoxicity by phenanthroline derivatives
    • Wang, L.; Wen, Y.; Liu, J.; Zhou, J.; Li, C.; Wei, C. Promoting the formation and stabilization of human telomeric G-quadruplex DNA, inhibition of telomerase and cytotoxicity by phenanthroline derivatives Org. Biomol. Chem. 2011, 9, 2648-2653
    • (2011) Org. Biomol. Chem. , vol.9 , pp. 2648-2653
    • Wang, L.1    Wen, Y.2    Liu, J.3    Zhou, J.4    Li, C.5    Wei, C.6
  • 18
    • 43049090109 scopus 로고    scopus 로고
    • Isoxazolone based inhibitors of p38 MAP kinases
    • Laufer, S. A.; Margutti, S. Isoxazolone based inhibitors of p38 MAP kinases J. Med. Chem. 2008, 51, 2580-2584
    • (2008) J. Med. Chem. , vol.51 , pp. 2580-2584
    • Laufer, S.A.1    Margutti, S.2
  • 19
    • 84885353210 scopus 로고    scopus 로고
    • U.S. Patent US2007/219195 A1
    • Goldstein, D. M.; Rueth, M. U.S. Patent US2007/219195 A1, 2007.
    • (2007)
    • Goldstein, D.M.1    Rueth, M.2
  • 23
    • 84858343513 scopus 로고    scopus 로고
    • Design of novel tyrosine-nitrogen mustard hybrid molecules active against uterine, ovarian and breast cancer cell lines
    • Descoîteaux, C.; Brasseur, K.; Leblanc, V.; Parent, S.; Asselin, é.; Bérubé, G. Design of novel tyrosine-nitrogen mustard hybrid molecules active against uterine, ovarian and breast cancer cell lines Steroids 2012, 77, 403-412
    • (2012) Steroids , vol.77 , pp. 403-412
    • Descoîteaux, C.1    Brasseur, K.2    Leblanc, V.3    Parent, S.4    Asselin, É.5    Bérubé, G.6
  • 25
    • 0037154817 scopus 로고    scopus 로고
    • Selective mono-C-methylations of arylacetonitriles and arylacetates with dimethylcarbonate: A mechanistic investigation
    • Tundo, P.; Selva, M.; Perosa, A.; Memoli, S. Selective mono-C-methylations of arylacetonitriles and arylacetates with dimethylcarbonate: A mechanistic investigation J. Org. Chem. 2002, 67, 1071-1077
    • (2002) J. Org. Chem. , vol.67 , pp. 1071-1077
    • Tundo, P.1    Selva, M.2    Perosa, A.3    Memoli, S.4
  • 26
    • 84858143592 scopus 로고    scopus 로고
    • Phosgene-free carbamoylation of aniline via dimethyl carbonate
    • Grego, S.; Aricò, F.; Tundo, P. Phosgene-free carbamoylation of aniline via dimethyl carbonate Pure Appl. Chem. 2012, 84, 695-705
    • (2012) Pure Appl. Chem. , vol.84 , pp. 695-705
    • Grego, S.1    Aricò, F.2    Tundo, P.3
  • 27
    • 84858111765 scopus 로고    scopus 로고
    • Cyclization reaction of amines with dialkyl carbonates to yield 1,3-oxazinan-2-ones
    • McElroy, C. R.; Aricò, F.; Benetollo, F.; Tundo, P. Cyclization reaction of amines with dialkyl carbonates to yield 1,3-oxazinan-2-ones Pure Appl. Chem. 2012, 84, 707-719
    • (2012) Pure Appl. Chem. , vol.84 , pp. 707-719
    • McElroy, C.R.1    Aricò, F.2    Benetollo, F.3    Tundo, P.4
  • 29
    • 84885345214 scopus 로고    scopus 로고
    • Asahi Kasei Chemicals Corporation. Patent WO2007/34669 A1
    • Asahi Kasei Chemicals Corporation. Patent WO2007/34669 A1, 2007.
    • (2007)
  • 30
    • 0003601534 scopus 로고
    • Ed. Merck and Co. Inc. Whitehouse Station, NJ
    • Budavari, S., Ed.; The Merck Index; Merck and Co., Inc.: Whitehouse Station, NJ, 1989.
    • (1989) The Merck Index
    • Budavari, S.1
  • 31
    • 84857176848 scopus 로고    scopus 로고
    • 5-Membered N-heterocyclic compounds by dimethyl carbonate chemistry
    • Aricò, F.; Toniolo, U.; Tundo, P. 5-Membered N-heterocyclic compounds by dimethyl carbonate chemistry Green Chem. 2012, 14, 58-61
    • (2012) Green Chem. , vol.14 , pp. 58-61
    • Aricò, F.1    Toniolo, U.2    Tundo, P.3
  • 32
    • 84864705754 scopus 로고    scopus 로고
    • Synthesis of five-membered cyclic ethers by reaction of 1,4-diols with dimethyl carbonate
    • Aricò, F.; Tundo, P.; Maranzana, A.; Tonachini, G. Synthesis of five-membered cyclic ethers by reaction of 1,4-diols with dimethyl carbonate ChemSusChem 2012, 5, 1578-1586
    • (2012) ChemSusChem , vol.5 , pp. 1578-1586
    • Aricò, F.1    Tundo, P.2    Maranzana, A.3    Tonachini, G.4
  • 34
    • 84872333277 scopus 로고    scopus 로고
    • Dimethyl carbonate as a sacrificial molecule for the synthesis of 5-membered N- and O-heterocycles
    • Tundo, P.; Aricò, F. Dimethyl carbonate as a sacrificial molecule for the synthesis of 5-membered N- and O-heterocycles J. Chin. Chem. Soc. 2012, 59, 1375-1384
    • (2012) J. Chin. Chem. Soc. , vol.59 , pp. 1375-1384
    • Tundo, P.1    Aricò, F.2
  • 37
    • 0036738434 scopus 로고    scopus 로고
    • The chemistry of dimethyl carbonate
    • Tundo, P.; Selva, M. The chemistry of dimethyl carbonate Acc. Chem. Res. 2002, 35, 706-716
    • (2002) Acc. Chem. Res. , vol.35 , pp. 706-716
    • Tundo, P.1    Selva, M.2
  • 38
    • 39349094916 scopus 로고    scopus 로고
    • Reaction of the ambident electrophile dimethyl carbonate with the ambident nucleophile phenylhydrazine
    • Rosamilia, A. E.; Aricò, F.; Tundo, P. Reaction of the ambident electrophile dimethyl carbonate with the ambident nucleophile phenylhydrazine J. Org. Chem. 2008, 73, 1559-1562
    • (2008) J. Org. Chem. , vol.73 , pp. 1559-1562
    • Rosamilia, A.E.1    Aricò, F.2    Tundo, P.3
  • 39
    • 11144270583 scopus 로고    scopus 로고
    • Synthesis of methylethers by reaction of alcohols with dimethylcarbonate
    • Tundo, P.; Memoli, S.; Hérault, D.; Hill, K. Synthesis of methylethers by reaction of alcohols with dimethylcarbonate Green Chem. 2004, 6, 609-612
    • (2004) Green Chem. , vol.6 , pp. 609-612
    • Tundo, P.1    Memoli, S.2    Hérault, D.3    Hill, K.4
  • 40
    • 54949085087 scopus 로고    scopus 로고
    • Synthesis of dialkyl ethers by decarboxylation of dialkyl carbonates
    • Tundo, P.; Aricò, F.; Rosamilia, A. E.; Memoli, S. Synthesis of dialkyl ethers by decarboxylation of dialkyl carbonates Green Chem. 2008, 10, 1182-1189
    • (2008) Green Chem. , vol.10 , pp. 1182-1189
    • Tundo, P.1    Aricò, F.2    Rosamilia, A.E.3    Memoli, S.4
  • 41
    • 77953274673 scopus 로고    scopus 로고
    • Synthesis of carbamates by reaction of amines with dialkyl carbonates: Influence of leaving and entering groups
    • Tundo, P.; McElroy, C. R.; Aricò, F. Synthesis of carbamates by reaction of amines with dialkyl carbonates: influence of leaving and entering groups Synlett 2010, 10, 1567-1571
    • (2010) Synlett , vol.10 , pp. 1567-1571
    • Tundo, P.1    McElroy, C.R.2    Aricò, F.3
  • 42
    • 57249092759 scopus 로고    scopus 로고
    • Insight into the hard-soft acid-base properties of differently substituted phenylhydrazines in reactions with dimethyl carbonate
    • Rosamilia, A. E.; Aricò, F.; Tundo, P. Insight into the hard-soft acid-base properties of differently substituted phenylhydrazines in reactions with dimethyl carbonate J. Phys. Chem. B 2008, 112, 14525-14529
    • (2008) J. Phys. Chem. B , vol.112 , pp. 14525-14529
    • Rosamilia, A.E.1    Aricò, F.2    Tundo, P.3
  • 44
    • 79958830466 scopus 로고    scopus 로고
    • Styrene oxidation by hydrogen peroxide in ionic liquids: The role of the solvent on the competition between two Pd-catalyzed processes, oxidation and dimerization
    • Chiappe, C.; Sanzone, A.; Dyson, J. P. Styrene oxidation by hydrogen peroxide in ionic liquids: The role of the solvent on the competition between two Pd-catalyzed processes, oxidation and dimerization Green Chem. 2011, 13, 1437-1441
    • (2011) Green Chem. , vol.13 , pp. 1437-1441
    • Chiappe, C.1    Sanzone, A.2    Dyson, J.P.3
  • 45
    • 0033474499 scopus 로고    scopus 로고
    • Quaternary ammonium salts as alkylating agents in the synthesis of tertiary phosphine oxides
    • Zafinyan, S. A.; Khachatryan, R. A.; lndzhikyan, M. H. Quaternary ammonium salts as alkylating agents in the synthesis of tertiary phosphine oxides Russ. Chem. Bull. 1999, 48, 388-390
    • (1999) Russ. Chem. Bull. , vol.48 , pp. 388-390
    • Zafinyan, S.A.1    Khachatryan, R.A.2    Lndzhikyan, M.H.3
  • 46
    • 77949653230 scopus 로고
    • A simple, biogenetically modeled synthesis of 4-(methylthio)butyl thiocyanate: The reaction of thiocyanate anion with S-methyl-(1,n)-epithionium ions
    • Benn, M. H.; Vinod Singh, K. A simple, biogenetically modeled synthesis of 4-(methylthio)butyl thiocyanate: the reaction of thiocyanate anion with S-methyl-(1,n)-epithionium ions Can. J. Chem. 1986, 64, 940
    • (1986) Can. J. Chem. , vol.64 , pp. 940
    • Benn, M.H.1    Vinod Singh, K.2
  • 47
    • 33947348889 scopus 로고
    • Quaternary ammonium salts from bromopropyldialkylamines. V. Conversion of cyclic ammonium salts to linear polymers
    • Gibbs, M. Quaternary ammonium salts from bromopropyldialkylamines. V. Conversion of cyclic ammonium salts to linear polymers J. Am. Chem. Soc. 1935, 57, 1137-1139
    • (1935) J. Am. Chem. Soc. , vol.57 , pp. 1137-1139
    • Gibbs, M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.