110601-03-1Relevant academic research and scientific papers
Versatile Synthesis of Dihydroquinolines and Quinoline Quinones Using Cyclobutenediones. Construction of the Pyridoacridine Ring System
Zhang, Dawei,Llorente, Isidro,Liebeskind, Lanny S.
, p. 4330 - 4338 (2007/10/03)
1-BOC-2-lithio-1, 4-dihydropyridines were condensed with 3,4-disubstituted cyclobutenediones to produce 1,2-adducts. Neat thermolysis under oxygen-free conditions produced substituted 1,4-dihydroquinoline hydroquinones in which the tert-butoxy residue of the BOC group was displaced by a phenolic residue, generating an oxazolone ring that functioned to protect both rings of the dihydroquinoline hydroquinone from untimely oxidation. Oxidative aromatization with concomitant loss of the oxazolone ring was achieved using 2 equiv of o-chloranil in acetic acid and provided substituted quinoline quinones in good yields. By use of this strategy, a concise synthesis of the pyridoacridine ring system was achieved.
SYNTHESIS OF SUBSTITUTED 3-PYRIDINECARBOXALDEHYDES
Comins, Daniel L.,Herrick, James J.
, p. 2159 - 2164 (2007/10/02)
Treatment of 3-substituted 1-(phenoxycarbonyl)-1,2-dihydropyridines with Vilsmeier reagent (POCl3/DMF) gave 3-substituted 5-formyl-1-(phenoxycarbonyl)-1,2-dihydropyridines, which were aromatized with hot sulfur to provide 5-substituted 3-pyridinecarboxaldehydes. The formylation of 4-substituted 1-(phenoxycarbonyl)-1,4-dihydropyridines and subsequent aromatization gave 4-substituted 3-pyridinecarboxaldehydes.
REGIOSELECTIVE ADDITION OF NUCLEOPHILES TO 1-(PHENOXYCARBONYL)-3-TRIALKYLSTANNYLPYRIDINIUM SALTS
Comins, Daniel L.,Mantlo, Nathan B.
, p. 759 - 762 (2007/10/02)
The regioselectivity of nucleophilic addition to 1-(phenoxycarbonyl)-3-trialkylstannylpyridinium salts was studied.
