Naslov
Novel Tandem Reaction for the Synthesis of N'-Substituted 2-Imino-1, 3-oxazolidines from Vicinal (sec- or tert-)Amino Alcohol of Desosamine

Autori
Vujasinović, Ines ; Marušić Ištuk, Zorica ; Kapić, Samra ; Bukvić Krajačić, Mirjana ; Hutinec, Antun ; Đilović, Ivica ; Matković-Čalogović, Dubravka ; Kragol, Goran

Izvornik
European journal of organic chemistry (1434-193X) 14 (2011), 13; 2507-2518

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
macrocycles; amino alcohols; domino reactions; heterocycles

Sažetak
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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA