26332-63-8

Basic information

• Product Name: 4-methyl-2-phenyl-3,6-dihydro-2H-[1,2]oxazine
• Synonyms: 4-methyl-2-phenyl-3,6-dihydro-2H-[1,2]oxazine
• CAS NO: 26332-63-8
• Molecular Weight: 175.23
• Mol File: 26332-63-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 4-methyl-2-phenyl-3,6-dihydro-2H-[1,2]oxazine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-methyl-2-phenyl-3,6-dihydro-2H-[1,2]oxazine(26332-63-8)
• EPA Substance Registry System: 4-methyl-2-phenyl-3,6-dihydro-2H-[1,2]oxazine(26332-63-8)

Safety Data

• Hazardous Substances Data: 26332-63-8(Hazardous Substances Data)

Upstream product

• 586-96-9 Nitrosobenzene 
• 78-79-5 isoprene 
• 100-65-2 N-Phenylhydroxylamine 
• 71-43-2 benzene 
• 98-95-3 nitrobenzene 

Downstream Products

• 55110-58-2 3-methyl-1-phenyl-2,5-dihydro-1H-pyrrole 
• 26332-67-2 3-methyl-4-phenylamino-but-2-en-1-ol 

Relevant articles and documents

Synthesis of 3,6-Dihydro-2H-[1, 2]-Oxazines from Nitroarenes and Conjugated Dienes, Catalyzed by Palladium/Phenanthroline Complexes and Employing Phenyl Formate as a CO Surrogate

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-2H-[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.

Synthesis of oxazines and N-arylpyrroles by reaction of unfunctionalized dienes with nitroarenes and carbon monoxide, catalyzed by palladium-phenanthroline complexes

The reaction between an unfunctionalized conjugated diene and a nitroarene under CO pressure and at 100 °C, catalyzed by [Pd(Phen)2][BF4]2 (Phen = 1,10-phenanthroline), affords the corresponding hetero-Diels -Alder adduct (oxazine) in up to 91% yields in one pot. If the reaction mixture is then heated to 200 °C, the oxazines are converted into the corresponding N-arylpyrroles in good yields. Pressures as low as 5 bar can be employed, and 0.08% catalyst is sufficient to effect the transformation. The reaction can be equally run by employing the nitroarene or the diene as limiting agent and works well for nitroarenes bearing either electron-withdrawing or mildly electron-donating substituents. A moderate steric hindrance on the nitroarene (o-methyl) is well tolerated, but 1,4-disubstituted-1,3-dienes are not suitable substrates.