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The Synthesis of an N,N′‐ Diformylated 36‐Membered N 8 O 4 Oxaazamacrocycle
Author(s) -
Adams Harry,
Bastida Rufina,
Fenton David E.,
Mann Brian E.,
Valencia Laura
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199908)1999:8<1843::aid-ejoc1843>3.0.co;2-d
Subject(s) - chemistry , formamide , formylation , amine gas treating , hydrochloride , medicinal chemistry , organic chemistry , catalysis
N ‐formylation of a secondary aliphatic amine has been achieved through the in situ reaction of potassium o ‐nitrophenolate, generated from o ‐nitrophenol, K 2 CO 3 , KOH, and bis(2‐chloroethyl)amine hydrochloride in hot DMF. The initial product, N , N ‐bis[2‐(2‐nitrophenoxy)ethyl]formamide has been reduced to provide N , N ‐bis[2‐(2‐aminophenoxy)ethyl]formamide which after an Mn II ‐templated cyclocondensation reaction with 2,6‐diformylpyridine followed by reductive demetallation with NaBH 4 gives an N , N ′‐diformylated 36‐membered N 8 O 4 oxaazamacrocycle.