6-Chloroxanthosine 1, when activated towards nucleophilic displacement at the 6-C position by conversion into the corresponding 3-N-(2,4-dinitrophenyl) derivative 4, reacted with aq. (NH3)-N-15 to afford [6-N-15]-isoguanosine 3b in 81% overall yield. Catalytic hydrogenation (Pd/C) of 1 led in 60% yield to isoinosine 8; alternatively, this could be obtained in 88% overall yield through alkaline hydrolysis of triphenylphosphonium salt 6, synthesized from 1 by reaction with PPh(3). The reactivity of 1 was further explored by treating it with primary and secondary amines: the 6-N propylamino and the 6-N piperidinyl derivatives (5a and 5b, respectively) could thus both be prepared in more than 90% yield.

6-Chloroxanthosine as useful intermediate for efficient syntheses of [6-15N]-isoguanosine, isoinosine and other purine nucleoside analogues / DE NAPOLI, Lorenzo; A., Messere; Montesarchio, Daniela; Piccialli, Gennaro; Varra, Michela. - In: NUCLEOSIDES & NUCLEOTIDES. - ISSN 0732-8311. - ELETTRONICO. - 16:1-2(1997), pp. 183-191. [10.1080/07328319708002532]

6-Chloroxanthosine as useful intermediate for efficient syntheses of [6-15N]-isoguanosine, isoinosine and other purine nucleoside analogues

DE NAPOLI, LORENZO;MONTESARCHIO, DANIELA;PICCIALLI, GENNARO;VARRA, MICHELA
1997

Abstract

6-Chloroxanthosine 1, when activated towards nucleophilic displacement at the 6-C position by conversion into the corresponding 3-N-(2,4-dinitrophenyl) derivative 4, reacted with aq. (NH3)-N-15 to afford [6-N-15]-isoguanosine 3b in 81% overall yield. Catalytic hydrogenation (Pd/C) of 1 led in 60% yield to isoinosine 8; alternatively, this could be obtained in 88% overall yield through alkaline hydrolysis of triphenylphosphonium salt 6, synthesized from 1 by reaction with PPh(3). The reactivity of 1 was further explored by treating it with primary and secondary amines: the 6-N propylamino and the 6-N piperidinyl derivatives (5a and 5b, respectively) could thus both be prepared in more than 90% yield.
1997
6-Chloroxanthosine as useful intermediate for efficient syntheses of [6-15N]-isoguanosine, isoinosine and other purine nucleoside analogues / DE NAPOLI, Lorenzo; A., Messere; Montesarchio, Daniela; Piccialli, Gennaro; Varra, Michela. - In: NUCLEOSIDES & NUCLEOTIDES. - ISSN 0732-8311. - ELETTRONICO. - 16:1-2(1997), pp. 183-191. [10.1080/07328319708002532]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11588/155394
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