TY - JOUR
T1 - Reactivity of 6-methylthiopurin-8-ones. Properties of 6-methylsulphonylpurin-8-ones
AU - Bergmann, Felix
AU - Rahat, Miriam
AU - Tamir, Ilana
PY - 1974
Y1 - 1974
N2 - All 6-methylthiopurin-8-ones (except those bearing a 1-methyl substituent, which decompose) are converted by chlorine in methanol at 0° into the corresponding sulphones. In a series of N-methyl 6-methylthiopurin-8-ones, only the 1-methyl, the 1,9- and 3,9-dimethyl, and the 3,7,9-trimethyl derivatives undergo thiohydrolysis. In contrast, all the corresponding sulphones are attacked by hydrogen sulphide anion. A 6-methylsulphonyl substituent weakens basicity and increases the acid strength of purines. In 6-methylsulphonylpurin-8-one, anion formation follows the order N-9 → N-7. A 3-methyl substituent, by virtue of reduction of the ring current in the pyrimidine system, causes a diamagnetic shift of the 2-H signal.
AB - All 6-methylthiopurin-8-ones (except those bearing a 1-methyl substituent, which decompose) are converted by chlorine in methanol at 0° into the corresponding sulphones. In a series of N-methyl 6-methylthiopurin-8-ones, only the 1-methyl, the 1,9- and 3,9-dimethyl, and the 3,7,9-trimethyl derivatives undergo thiohydrolysis. In contrast, all the corresponding sulphones are attacked by hydrogen sulphide anion. A 6-methylsulphonyl substituent weakens basicity and increases the acid strength of purines. In 6-methylsulphonylpurin-8-one, anion formation follows the order N-9 → N-7. A 3-methyl substituent, by virtue of reduction of the ring current in the pyrimidine system, causes a diamagnetic shift of the 2-H signal.
UR - http://www.scopus.com/inward/record.url?scp=37049140727&partnerID=8YFLogxK
U2 - 10.1039/P19740000470
DO - 10.1039/P19740000470
M3 - ???researchoutput.researchoutputtypes.contributiontojournal.article???
AN - SCOPUS:37049140727
SN - 1472-7781
SP - 470
EP - 477
JO - Journal of the Chemical Society, Perkin Transactions 1
JF - Journal of the Chemical Society, Perkin Transactions 1
ER -