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Regioselectivity in S N H reactions of some 3‐nitro‐1,8‐naphthyridines with chloromethyl phenyl sulfone
Author(s) -
Grzegozek Maria,
Woźniak Marian,
Barański Andrzej,
Van Der Plas Henk C.
Publication year - 1991
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570280440
Subject(s) - chemistry , nitro , sulfone , regioselectivity , medicinal chemistry , nucleophile , yield (engineering) , substrate (aquarium) , organic chemistry , catalysis , alkyl , materials science , oceanography , metallurgy , geology
Abstract A number of 2‐X‐3‐nitro‐1,8‐naphthyridines (X= H,D,OH,Cl,NH 2 , OEt) react with the anion of chloromethyl phenyl sulfone exclusively into 2‐X‐3‐nitro‐4‐(phenylsulfonylmethyl)‐1,8‐naphthyridines in high yield. The reaction is found by quantum chemical calculations to be controlled by the interactions of the HOMO of the nucleophile with the LUMO of the substrate, and not by charge.