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Natural Product Research
Formerly Natural Product Letters
Volume 24, 2010 - Issue 1
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Original Articles

Effect of successive increase in alcohol chains on reaction with isocyanates and isothiocyanates

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Pages 18-23 | Received 10 Apr 2007, Accepted 08 Jul 2008, Published online: 09 Dec 2009

References

  • Aine, R. (2004). Paper Presentation at the Medical Polymers Meeting in Dublin, organised by Rapra Technology, 15–16 Nov 2004.
  • Ali , RM-A , Mohsen , R and Parisa , N . 2006 . Solvent free preparation of primary carbamates . Turkish Journal of Chemistry , 30 : 269 – 276 .
  • Baker , JW and Holdsworth , JB . 1947 . The mechanism of aromatic side-chain reaction with special reference to the polar effects of substituents. Part XIII . Journal of the Chemical Society , : 713 – 726 .
  • Bickel , VT and French , HE . 1926 . Alpha-naphthyl isocyanate as a reagent for alcohols . Journal of the American Chemical Society , 48 : 747 – 451 .
  • de Bont , DBA , Leenders , RGG , Haisma , HJ , van der Meulen-Muileman , I and Scheeren , HW . 1997 . Synthesis and biological activity of β-glucuronyl carbamate-based prodrugs of paclitaxel as potential candidates for ADEPT . Bioorganic and Medicinal Chemistry , 5 ( 2 ) : 405 – 414 .
  • Devdutt , C , Nisha , M and Virendra , M . 2007 . An efficient, one-pot synthesis of carbamates from the corresponding alcohols using Mitsunobu's reagent . Monatshefte fur Chemie/Chemical Monthly , 138 ( 1 ) : 57 – 60 .
  • Dibenedetto , A , Aresta , M , Fragale , C and Narracci , M . 2002 . Reaction of silylalkylmono- and silylakyldi-amines with carbon dioxide: Evidence of formation of inter- and intra-molecular ammonium carbamates and their conversion into organic carbamates of industrial interest under carbon dioxide catalysis . Green Chemistry , 4 : 439 – 443 .
  • Feldman , D and Barbalata , A . 1996 . Synthetic polymers, technology, properties, applications , 273 London : Chapman and Hall .
  • French , HE and Wirtel , AF . 1926 . Alpha-naphthylisocyanate as a reagent for phenols and aliphatic amines . Journal of the American Chemical Society , 48 : 1736 – 1739 .
  • Gaylord , NG and O’Brien , J . 1955 . Carbamates, II. Reactions of 2,4-diisocyanatotoluene . Recueil das Travaux Chimiques des Pays-Bas , 74 : 218 – 219 .
  • Gupte , SP , Shivarkar , AB and Chaudhari , RV . 2001 . Carbamate synthesis by solid-base catalyzed reaction of disubstituted ureas and carbonate . Journal of the Chemical Society–Chemical Communications , 2 : 2620 – 2621 .
  • Jhillu , SY , Basi , VSR and Garudammagari , SKKR . 2000 . Indium-mediated efficient conversion of azides to carbamates . New Journal of Chemistry , 24 : 571 – 573 .
  • Jose, A. (1995). Dioxolenylmethyl carbamates pro moieties for amine drugs. US Patent No. 5,466,811.
  • Jose , A , Robyn , C , Stuart , RM and Harvey , S . 1988 . (Acyloxy) alkyl carbamates as novel bioreversible prodrugs for amines: Increased permeation through biological membranes . Journal of Medicinal Chemistry , 31 : 318 – 322 .
  • Jose , A , Robert , AF , Judith , AB , Barbara , AP and Evamarie , CG . 1991 . (Acyloxy) alkyl carbamate prodrugs of norfloxacin . Journal of Medicinal Chemistry , 34 : 78 – 81 .
  • Ken , JB . 1994 . Carbamates esters: A simple, mild method of formation . Synlett , 2 : 825 – 826 .
  • Kim, H.S., Lee, S.D., Lee, H.-J., Seo, I.-S., & Kim, Y.J. (1999) Method for preparation of carbamates. US Patent No. 5,962,721.
  • Motolcsy , G , Nadasy , M and Andriska , V . 1988 . Pesticide chemistry , 90 Budapest : Academiai Kiado .
  • Neuberg , C and Kansky , E . 1909 . Reduction of amino acids to amino aldehydes . Biochemical Zeit , 20 : 446 – 462 .
  • NTP (National Toxicology Program) (2005). NIEHS, National Institutes of Health, ‘Eleventh Report on Carcinogens, Urethane’. Retrieved May 13, 2006 from http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s184uret.pdf
  • Parcell, R. (1958a). Piperazine derivatives and process. US Patent No. 2,836,595.
  • Parcell , R . 1958b . Piperazine derivatives . Chemical Abstracts , 52 : 20215
  • Pietro , T , Salima , B , Alessandro , L and Gabriel , S . 2005 . Direct synthesis of N-methylurethanes from primary amines with dimethyl carbonate . Pure and Applied Chemistry , 77 ( 10 ) : 1719 – 1725 .
  • Leenders , RGG , Gerrits , KAA , Ruijtenbeek , R , Scheeren , HW , Haisma , HJ and Boven , E . 1995 . β-Glucuronyl based promoieties designed for prodrugs in ADEPT . Tetrahedron Letters , 36 ( 10 ) : 1701 – 1704 .
  • Saunders , JH and Slocombe , RJ . 1948 . The chemistry of the organic isocyanates . Chemical Reviews , 43 : 203 – 218 .
  • Shahnaz , P , Syed , MAH , Rashid , AK , Khalid , MK , Nighat , A and Tahira , BS . 2005 . An expeditious method for the synthesis of symmetrical 1,3-disubstituted ureas and thioureas . Synthetic Communications , 35 : 1663 – 1674 .
  • Shinsuke , F , Masazumi , C and Masashi , K . 1984 . A novel catalytic synthesis of carbamates by oxidative alkoxycarbonylation of amines in the presence of palladium and iodide . Journal of the Chemical Society–Chemical Communications , 2 : 399 – 400 .
  • Shoichiro , O . 1972 . Recent advances in isocyanate chemistry . Chemical Reviews , 72 ( 5 ) : 457 – 496 .
  • Smith , HA . 1968 . Effect of urethane groups on the reaction of alcohols with isocyanates . Journal of Polymer Science Part A-1: Polymer Chemistry , 6 ( 5 ) : 1299 – 1306 .
  • Syed , MAH , Shahnaz , P , Rashid , AK , Khalid , MK and Nighat , A . 2003 . Tertiary amines promoted synthesis of symmetrical 1,3-disubstituted ureas . Natural Product Research , 17 : 351 – 354 .
  • Syed , MR , James , EH , Brendan , CB , Donald , RM , Richard , RT and David , WB . 1999 . Prodrugs for amidines: Synthesis and anti-Pneumocystis carinii activity of carbamates of 2,5-bis(4-amidinophenyl) furan . Journal of Medicinal Chemistry , 42 : 3994 – 4000 .
  • Thompson , A . 2002 . Pest control on field vegetables threatened by the loss of organophosphorus (OP) and carbamate insecticides? . Pesticide Outlook , 13 : 84 – 86 .
  • VCU (Virginia Commonwealth University) (2006). The Chemical/Biological Safety Section (CBSS) of the Office of Environmental Health and Safety, ‘Working with Urethane’. Retrieved May 13, 2006 from http://www.vcu.edu/oehs/chemical/biosafe/urethane.pdf
  • Zhong , L , Panayota , B , Stanley , AL Jr and Yang-I. , L . 1997 . Synthesis of (alkoxycarbonyloxy) methyl, (acyloxy) methyl and (oxodioxolenyl) methyl carbamates as bioreversible prodrug moieties for amines . Bioorganic and Medicinal Chemistry Letters , 7 ( 22 ) : 2909 – 2912 .

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