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

作者：Vujasinovic Ines; Istuk Zorica Marusic; Kapic Samra; Krajacic Mirjana Bukvic; Hutinec Antun; Dilovic Ivica; Matkovic Calogovic Dubravka; Kragol Goran^*

来源：European Journal of Organic Chemistry, 2011, 2011(13): 2507-2518.

DOI：10.1002/ejoc.201001707

• Macrocycles
• Amino alcohols
• Domino reactions
• Heterocycles

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 physico-chemical and hence biological properties of these new molecules.

• 出版日期2011-5