Unusual patterns of reactivity in the photolysis of a substituted 4-acetylquinoline

Epling, Gary A.; Ayengar, Narayan K. N.; McCarthy, Eugene F.

doi:10.1016/s0040-4039(01)92682-6

Cited by 5 publications

(2 citation statements)

References 9 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…(1 H, dd, Jtrans = 17 Hz, Jgem = 1.5 Hz, C-21H), 5.37 (1 H, dd, Jc¡a = 10.5 Hz, Jgem = 1.5 Hz, C-21 H), 5.97 (1 H, dd, Jtrans = 17 Hz, Jcia = 10.5 Hz, C-20 H), 6.62-7.23 ppm (3 H, aromatic protons).7 Anal. Caled for C23H27F303 (408.5): C, 67.63; H, 6.66; F, 13.95.…”

mentioning

confidence: 99%

“…Caled for C23H27F303 (408.5): C, 67.63; H, 6.66; F, 13.95. Found: C, 68.27; H, 6.82; F, 13.96. Solvolysis of 2 in HMPT in the presence of NaNg in the same conditions as for 1 gave 0.17 gofa residue (from 0.20 g of 2) which was chromatographed on PLC [benzene-n-hexane (1:2) as eluant] to afford 0.14 g (82%) of (E)-3-methoxy-21-azido-19-norpregna-I, 3,5 (10),17(20)-tetraene (2b) as an oil, pure by NMR analysis: [«] o +51°(c 4.0); IR (N3) 2100 cm-1; NMR 0.81 (3 H, s. 13-Me), 3.73 (2 H, d, J = 7 Hz, CH2N3), 3.74 (3 H, s, 3-OMe),5.23 (1 H, tt, J = 1, 2 Hz, C-20 H), 6.62-7.27 (3 H, aromatic protons).7 Anal. Caled for C21H27N3O (337.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Photochemical reduction and decarboxylation of 2-phenylquinoline-4-carboxylic acids

Epling¹,

Ayengar²,

Lopes³

et al. 1978

J. Org. Chem.

Self Cite

View full text Add to dashboard Cite

NotesFrom a synthetic point of view methanolysis of 1 (and likely similar unimolecular solvolyses) appears to be of limited usefulness. Solvolysis of 1 and 2 in aprotic solvents in the presence of strong nucleophiles should conversely represent a good alternative to the displacement of analogous 21-chloro derivatives lg2 and 2c5 for the introduction of substituents at C-21. Experimental Section617a-Pregna-5,20-dien-3/S,17-diol 3-Acetate 17-Trifluoroacetate (1). A solution of 17a-pregna-5,20-dien-3/3,17-diol 3-acetate (la)2 (0.36 g, 1 mmol) in pyridine (1.7 mL) was treated with trifluoroacetic anhydride (0.7 mL) at 0 °C for 15 min. Then cold 1 N HC1 (11.7 mL) was added and the mixture was extracted with ether. The ether layers were washed to neutrality with cold water, dried (Na2S04), and evaporated. The residue (0.45 g) was crystallized from n-hexane (0.33

show abstract

mentioning

confidence: 99%

mentioning

confidence: 99%