N–N Bond-Forming Cyclization for the One-Pot Synthesis of N-Aryl[3,4-d]pyrazolopyrimidines | Zendy

Lindsay E. Evans | Zendy; Matthew D. Cheeseman | Zendy; Keith Jones | Zendy

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N–N Bond-Forming Cyclization for the One-Pot Synthesis of N-Aryl[3,4-d]pyrazolopyrimidines

Author(s) -

Lindsay E. Evans,

Matthew D. Cheeseman,

Keith Jones

Publication year - 2012

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol301561a

Subject(s) - chemistry , hydroxylamine , oxime , yield (engineering) , aryl , medicinal chemistry , hydroxylamine hydrochloride , combinatorial chemistry , amination , organic chemistry , catalysis , materials science , alkyl , metallurgy

An efficient one-pot synthesis of N-aryl[3,4-d]pyrazolopyrimidines in good yield and under mild reaction conditions is described. By exploiting electron-deficient hydroxylamines, the substituted oxime products were formed with very high E-diastereoselectivity. The key step utilizes a cyclization reaction upon an oxime derived from hydroxylamine-O-sulfonic acid to form the N-N bond of the product.

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