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Novel Tandem Reaction for the Synthesis of N ′‐Substituted 2‐Imino‐1,3‐oxazolidines from Vicinal ( sec ‐ or tert ‐)Amino Alcohol of Desosamine
Author(s) -
Vujasinović Ines,
Marušić Ištuk Zorica,
Kapić Samra,
Bukvić Krajačić Mirjana,
Hutinec Antun,
Đilović Ivica,
MatkovićČalogović Dubravka,
Kragol Goran
Publication year - 2011
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/ejoc.201001707
Subject(s) - chemistry , thiourea , tandem , yield (engineering) , vicinal , alkylation , alcohol , oxazolidine , cascade reaction , combinatorial chemistry , organic chemistry , stereochemistry , medicinal chemistry , catalysis , materials science , metallurgy , composite material
Two one‐pot methods, sequential and tandem, for the preparation of N ′‐substituted 2‐imino‐1,3‐oxazolidines from the vicinal ( sec ‐ or tert )‐amino alcohol of desosamine via intermediary alkyl‐, aryl‐, heteroaryl‐, and heteroalkyl‐thiourea moieties are described. Particularly interesting is the novel one‐pot tandem reaction of the vicinal tert ‐amino alcohol that involves dealkylation, thiourea formation, and a final cyclization to yield 2‐imino‐1,3‐oxazolidine structures. The yields of both one‐pot methods are comparable to the yield of the sequential reaction. A small library of a new class of desosamine‐modified 14‐ and 15‐membered macrolides was prepared to demonstrate the variety of substituents that can be easily introduced and thus enable a huge variation of the physicochemical and hence biological properties of these new molecules.