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Tên Synthesis of 1-Alkyl-2-(trifluoromethyl)azetidines and Their Regiospecific Ring Opening toward Diverse α-(Trifluoromethyl)Amines via Intermediate Azetidinium Salts
Lĩnh vực Hóa - Công nghệ thực phẩm
Tác giả Sara Kenis, Matthias D’hooghe, Guido Verniest, Tuyet Anh Dang Thi, Phạm Thế Chính, Tuyen Van Nguyen, and Norbert De Kimpe
Nhà xuất bản / Tạp chí The Journal of Organic Chemistry (JOC) - American Chemical Society (SCI, IF=4.45) Tập 77 Số 14 Năm 2012
Số hiệu ISSN/ISBN ISSN: 0022-3263
Tóm tắt nội dung

A convenient approach toward nonactivated 1-alkyl-2-(trifluoromethyl)azetidines as a new class of constrained azaheterocycles was developed starting from ethyl 4,4,4-trifluoroacetoacetate via imination, hydride reduction, chlorination, and base-induced ring closure. Furthermore, the reactivity profile of these 2-CF -azetidines was assessed by means of quaternization and subsequent regiospecific ring opening at C4 of the azetidinium intermediates by oxygen, nitrogen, carbon, sulfur, and halogen nucleophiles, pointing to a clear difference in reactivity compared to azetidines bearing other types of electronwithdrawing groups at C2.

( (http://pubs.acs.org/doi/abs/10.1021/jo300694y

 

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