Synthesis and study of the properties of 4-substituted 3-aminomethylcoumarins

Savel’ev, V. L.; Artamonova, O. S.; Troitskaya, V. S.; Shavyrina, V. V.; Afanas'eva, T. G.; Zagorevskii, V. A.

doi:10.1007/bf00568940

Cited by 4 publications

(2 citation statements)

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“…13 C NMR (CDCl 3 ), δ: 12.14 (CH 2 Me); 45.48 (CH 2 Me); 95.96 (C(3)); 116.99 (C(10)); 117.89 (C(8)); 123.10 (C(5)); 125.03 (C(6)); 131.19 (C(7)); 154.31 (C(9)); 159.36 (C(4)); 162.79 (C = O). Compound 14 has been synthesized earlier, 16 (8)). 13 …”

Section: Methodsmentioning

confidence: 99%

Synthesis of 4-aminopolymethoxycoumarins from 4-hydroxycoumarin triflates

et al. 2006

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Section: Methodsmentioning

confidence: 99%

Synthesis of 4-aminopolymethoxycoumarins from 4-hydroxycoumarin triflates

et al. 2006

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“…6 Interestingly, even enolate anion of 4-hydroxycoumarin exhibits similar spectrum, with three maxima in the long-wavelength region; 278 nm (⑀ 10,470), 286 nm (⑀ 13,500), and at 297 nm (⑀ 12,000). 29 According to Person et al 30 the occurrence of exciton coupling requires noncoplanar arrangement of the four points that define two transition dipols, A-B, and C-D, in Figure 9. This prerequisite is satisfied in 7 (Fig.…”

Section: Chiroptical Properties and Absolute Configurationmentioning

confidence: 99%

Long-distance control in stereoselective reduction of 3-[3-(4?-bromo[1,1?-biphenyl]-4-yl)-3-keto-1-phenylpropyl]-4-hydroxy-2H-1-benzopyran-2-one: Relative configuration of prevailing diastereomer and absolute configuration of its enantiomers

Avdagić

Cotarca²,

Hameršak

et al. 1997

Chirality

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Depending on the reducing agent and reaction conditions, diastereoselective reduction of 3‐[3‐(4′‐bromo[1,1′‐biphenyl]‐4‐yl)‐3‐keto‐1‐phenylpropyl]‐4‐hydroxy‐2H‐1‐benzopyran‐2‐one (2) proceeds with different stereoselectivity; a surprisingly high, approximately 90% d.e. of 4A is achieved with NaBH4 in MeOH at low temperature. Resulting diastereomeric racemates 4A and 4B are separated and their respective syn and anti configurations are assigned on the bases of mechanic considerations, supported by the 1H‐NMR spectra and conformational analysis based on MM2 calculations. The syn diastereomer 7A, 4‐OMe derivative of 4A, was partially resolved by acylation at C(3)‐OH with S‐(−)‐camphanic acid to camphanyl ester 12 of (−)‐7A, leaving (+)‐enantiomer 7A. The assignment of absolute 1R,3S‐configuration to (−)‐7A is based on comparison of its CD spectrum with those of the model compounds S‐14 and R‐15, which represent partial chromophores 4‐hydroxy‐2H‐1‐benzopyran‐2‐one (4‐hydroxycoumarin) A, and 4′‐bromo‐1,1′‐biphenyl B; their exciton coupling in (−)‐7A is suggested. Chirality 9:512–522, 1997. © 1997 Wiley‐Liss, Inc.

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