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Synthesis of 3,6‐Dihydro‐2 H ‐[1, 2]‐Oxazines from Nitroarenes and Conjugated Dienes, Catalyzed by Palladium/Phenanthroline Complexes and Employing Phenyl Formate as a CO Surrogate
Author(s) -
ELAtawy Mohamed A.,
Formenti Dario,
Ferretti Francesco,
Ragaini Fabio
Publication year - 2018
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201801223
Subject(s) - oxazines , palladium , chemistry , catalysis , phenanthroline , formate , conjugated system , adduct , medicinal chemistry , carbon monoxide , methyl formate , decomposition , photochemistry , organic chemistry , combinatorial chemistry , polymer
Palladium/phenanthroline catalyzed reduction of nitroarenes by in situ‐generated carbon monoxide, from the decomposition of phenyl formate, affords the corresponding nitrosoarenes. The latter are trapped by conjugated dienes to give the corresponding 3,6‐dihydro‐2 H ‐[1, 2]‐oxazines (hetero Diels‐Alder adducts). Many functional groups are well tolerated. Yields are higher than those obtainable by any previously reported method, including the direct reaction of the diene with the pure nitrosoarene. The reaction can be performed in a single standard glass pressure tube, without the need for autoclaves or high‐pressure CO lines.