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Low-Valent Titanium Induced Carbonyl Coupling Reactions

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R 1<br />

R 2<br />

N<br />

CH 3<br />

Table 9. <strong>Titanium</strong> induced synthesis of zindoxifen and analogues<br />

R 4<br />

R 1 R 2 R 3 R 4<br />

67a OAc H OAc Et<br />

67b OH H OH Et<br />

67c OH OH OH Me<br />

67d<br />

OMe OMe OMe Me<br />

1.5 Synthesis of 2-Quinolones<br />

68<br />

R 1<br />

NH<br />

O<br />

O<br />

O<br />

R 2<br />

TiCl 3/Zn<br />

THF , reflux<br />

Table 10. <strong>Low</strong>-valent titanium induced 2-quinolone synthesis<br />

Entry Yield (%)<br />

1<br />

2<br />

R 1 R2<br />

H<br />

R 3<br />

Me Ph 80<br />

3 Ph Ph 68<br />

4 Ph Me 69<br />

5 Me 2-Thienyl 50<br />

6 OMe OH 41<br />

Ph<br />

64<br />

69<br />

R 1<br />

N<br />

H<br />

R 2<br />

O<br />

31

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