49805-30-3Relevant articles and documents
Unusual mechanism of hydrolysis of the tosyl cyanide-cyclopentadiene adduct to the lactam 2-azabicyclo[2.2.1]hept-5-en-3-one
Morgan, Paul E.,McCague, Ray,Whiting, Andrew
, p. 1811 - 1812 (1996)
Hydrolysis of the cycloaddition product derived from tosyl cyanide and cyclopentadiene was investigated using 18O label incorporation experiments; thus, sulfonyl imine 2 was transformed into 18O labelled lactam 3 with 18O labelled acetic acid, which is consistent with the intervention of intermediate 6 during the hydrolysis.
Carbovir-related compounds and phosphonate analogues
Pham, Phuong-T.,Vince, Robert
, p. 779 - 791 (2007)
Detailed syntheses of carbovir-related cis-[2-(9H-Purin-9-yl)-3- cyclopentene]-1-methanols and phosphonates of selected analogues are presented. Our interest in this chemistry stems from antiviral activity shown by closely related compounds. Access to the key β-lactam was achieved by the reaction of monocyclopentadiene with chlorosulfonyl isocyanate at -78°C rather than at the reported1 ambient temperature, where only the less ring-strained and more stable γ-lactam is formed. Copyright Taylor & Francis Group, LLC.
Substituted cyclopentane and cyclopentene compounds useful as neuraminidase inhibitors
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, (2008/06/13)
Compounds I-III wherein U is CH, O, or S; Z is mono- or di-substituted carbon; R is (CH2)nCO2H, (CH2)nSO3H, (CH2)nPO3H2, (CH2)nNO2, CH(SCH3)3, esters; R1 is H, hydroxyalkyl, aminoalkyl, alkoxyalkyl; RR1 is O; n is 0-4; R2, R3 is H, hydroxyalkyl, aminoalkyl, alkoxyalkyl, haloalkyl; R4 is (CH2)nOH, (CH2)nNH2, substituted alkyl were prepd. as neuraminidase inhibitors. Thus, (1R,3R,4R,1′S)-(?)-(1′-acetylamino-2 ′-ethyl)butyl-4-(aminoimino)methylaminocyclopentan-1-carboxylic acid was prepd. and tested in vitro as neuraminidase inhibitor (IC501μM).
Process for producing 2-azabicyclo[2.2.1]hept-5-en-3-one
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, (2008/06/13)
2-Azabicyclo[2.2.1]hept-5-en-3-one is prepared by a process comprising: continuously mixing a substituted sulfonyl cyanide represented by formula (I): R—SO2CN??(I), wherein R represents an alkyl group or a phenyl group or a substituted phenyl group, with cyclopentadiene; and then continuously adding the resultant reaction solution to water or to a mixed solvent comprising water and a hydrocarbon solvent under the condition that the pH of the present reaction mixture ranges from 4 to 7.