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Isomerizable (E/Z)-alkynyl-O-methyl oximes employing TMSCl–NCS in chlorinative cyclization for the direct synthesis of 4-chloroisoxazoles
- Source :
- RSC Advances. 6:48666-48675
- Publication Year :
- 2016
- Publisher :
- Royal Society of Chemistry (RSC), 2016.
-
Abstract
- For the first time, 4-chloroisoxazoles are directly synthesized in moderate to excellent yields from (E/Z)-alkynyl-O-methyl oximes via chlorinative cyclization. The synthesis employs the combination of N-chlorosuccinimide (NCS) and chlorotrimethylsilane (TMSCl) in nitromethane solvent where chlorine (Cl2) and hydrochloric acid (HCl) are generated in situ. In addition, the current protocol is applicable to the synthesis of 4-bromo- and 4-iodoisoxazoles when N-bromosuccinimide (NBS) and N-iodosuccinimide (NIS), respectively, are employed in place of NCS. The current method can improve the overall efficiency of the preparation of 4-haloisoxazoles starting from the step where alkynyl-O-methyl oximes are prepared since (E)-isomers can isomerize and cyclize under the conditions.
- Subjects :
- Nitromethane
010405 organic chemistry
General Chemical Engineering
chemistry.chemical_element
Hydrochloric acid
General Chemistry
010402 general chemistry
01 natural sciences
Combinatorial chemistry
0104 chemical sciences
Solvent
chemistry.chemical_compound
chemistry
Chlorine
Organic chemistry
Overall efficiency
Subjects
Details
- ISSN :
- 20462069
- Volume :
- 6
- Database :
- OpenAIRE
- Journal :
- RSC Advances
- Accession number :
- edsair.doi...........cee60e78bf26252342aabdbb3380cad6