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Synthesis of Naphthoxazoles by Photocyclization of 4‐/5‐(Phenylethenyl)oxazoles
Author(s) -
Šagud Ivana,
ŠindlerKulyk Marija,
Škorić Irena,
Kelava Vanja,
Marinić Željko
Publication year - 2018
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.201800737
Subject(s) - chemistry , reagent , phosphonium , aryl , wittig reaction , combinatorial chemistry , isocyanide , medicinal chemistry , photochemistry , organic chemistry , alkyl
Promising test results on the biological activity of our previously described naphtho[1,2‐ d ]oxazoles and heterobenz[1,2‐ d ]oxazoles, obtained by the photochemical cyclization of 5‐phenylethenyl‐ and 5‐heteroarylethenyloxazoles, prompted us to continue with the photochemical synthesis of substituted naphtho[1,2‐ d ]oxazoles, and to extend the photochemical cyclization to the synthesis of naphtho/heterobenz[2,1‐ d ]oxazoles from 4‐(aryl/heteroarylethenyl)oxazoles. The required p ‐ and o ‐phenyl‐substituted 5‐arylethenyloxazoles were prepared from the corresponding α,β‐unsaturated aldehydes and the TosMIC reagent (tosylmethyl isocyanide) by the Van Leusen reaction. The substituted 4‐(aryl/heteroarylethenyl)oxazoles were prepared by the Wittig reaction starting from various phosphonium salts and 2‐H/methyl‐4‐oxazolecarbaldehydes.