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7‐Substituted 7‐Deaza‐2′‐deoxyguanosines: Regioselective Halogenation of Pyrrolo[2,3‐ d ]pyrimidine Nucleosides
Author(s) -
Ramzaeva Natalya,
Seela Frank
Publication year - 1995
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19950780505
Subject(s) - chemistry , regioselectivity , halogenation , pyrimidine , deoxyguanosine , derivative (finance) , stereochemistry , diastereomer , medicinal chemistry , organic chemistry , catalysis , financial economics , adduct , economics
The synthesis of 7‐chloro‐, 7‐bromo‐, and 7‐iodo‐substituted 7‐deaza‐2′‐deoxyguanosine derivatives 2b – d is described. The regioselective 7‐halogenation with N ‐halogenosuccinimides was accomplished using 7‐[2‐deoxy‐3,5‐ O ‐di(2‐methylpropanoyl)‐β‐ D ‐ erythro ‐ pentofuranosyl]‐2‐(formylamino)‐4‐methoxy‐7 H ‐pyrrolo[2,3‐ d ]‐ pyrimidine ( 4 ) as the common precursor. A one‐pot reaction (2 N aq. NaOH) of the halogenated intermediates 5a – c furnished the desired compounds. Also the 7‐hexynyl derivative 2e of 7‐deaza‐2′‐deoxyguanosine is described.