700-79-8Relevant articles and documents
Reactions of 3-Benzoyl-3,4-dihydro-2-methyl-4-quinazolinecarbonitrile (2-Methylquinazoline Reissert Compound) with Acid, Base, Sodium Hydride, and Electrophiles
Higashino, Takeo,Sato, Susumu,Suge, Hiroki,Tanji, Ken-Ichi,Miyashita, Akira,Katori, Tatsuhiko
, p. 930 - 939 (2007/10/02)
Acid hydrolysis of 3-benzoyl-3,4-dihydro-2-methyl-4-quinazolinecarbonitrile (11, 2-methylquinazoline Reissert compound) resulted in the formation of the oxazole (13).Alkaline hydrolysis gave 2-methylquinazoline (12) and banzoic acid (8).The anion (D1), generated from 11 and NaH in dimethylformamide (DMF), underwent decomposition to give the ketone (14) and the cyanoquinazoline (15) together with by-products 12 and O-benzoylbenzoin (9).Compound 11 reacted with aromatic aldehydes (10a-c) in the presence of NaH to give the benzoates (16a-c) and by-products 12 and 15.Alkylation (or arylation) with alkyl (or aryl) halides (11a, b) afforded the corresponding 4-substituted derivatives (19a, b) and a by-product 14.The reactivities of 11 and 3-benzoyl-3,4-dihydro-4-quinazolinecarbonitrile (21, quinazoline Reissert compound) are compared. Keywords---Reissert compound; quinazoline; hydrolysis; Reissert compound anion; rearrengement; aromatization; electronic effect; electrophilic substitution
Photostimulated Reactions of 2-Bromopyridine and 2-Chloroquinoline with Nitrile-Stabilized Carbanions and Certain Other Nucleophiles
Moon, Marcus P.,Komin, Andrew P.,Wolfe, James F.,Morris, Gene F.
, p. 2392 - 2399 (2007/10/02)
Potassiophenylacetonitrile (2) reacts with 2-bromopyridine (1) and 2-chloroquinoline (4) via the SRN1 mechanism when the reactants are exposed to near-UV light in liquid NH3.Potassioacetonitrile (6) reacts similarly with 1 and 4 upon photostimulation; however, the photo-SRN1 reaction with 1 is accompanied by SNAr2 amination which becomes the major reaction in the dark or in the presence of di-tert-butyl nitroxide.Substrate 4 undergoes competing SNAr2 amination with amide ion to form 2-aminoquinoline (10) and SN(ANRORC) reactions with both amide ion and carban ion 6 to form 3-methylquinazoline (11) and 2-methyl-3-cyanoquinoline (12), respectively.Formation of 12 becomes the major pathway in reactions between 4 and 6 carried out in the dark. 4-Picolylpotassium (14) reacts with 1, 4, and 4-bromopyridinium chloride (16) under photostimulation to form the appropriate dihetarylmethanes, along with the corresponding amino heterocycles.Amination of 1, 4, and 16 predominates when these reactions are carried out in the dark.Ammonium thiophenoxide (20) undergoes a slow photo-SRN1 reaction with 1 but fails to produce the expected 2-quinolyl phenyl sulfide with 4 after 2 h of irradiation.Potassium salts of acetylene, phenylacetylene, and phthalimide do not react with 1 or 4 after 2 h of exposure to near-UV light.