Side??Chain Retention During Lithiation of 4??Picoline and 3, 4??Lutidine: Easy Access to Molecular Diversity in Pyridine Series

T Kaminski, P Gros, Y Fort

Index: Kaminski, Thomas; Gros, Philippe; Fort, Yves European Journal of Organic Chemistry, 2003 , # 19 p. 3855 - 3860

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Citation Number: 23

Abstract

Abstract The first direct ring-selective lithiation of 4-picoline and 3, 4-lutidine has been achieved through the use of BuLi/LiDMAE aggregates to prevent the usual side-chain metallation. Several functionalities have been introduced at the C-2, C-6 and C-5 positions by ring-selective sequential lithiation, opening a simple and fast route to polysubstituted pyridine building blocks.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, ...

 Related Synthetic Route
4-Picoline Structure

108-89-4

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1N1&VR Structure

611-74-5

1N1&VR

~80%

(4-methylpyridin-2-yl)-phenylmethanone Structure

18103-77-0

(4-methylpyridi...

4-Picoline Structure

108-89-4

4-Picoline

~70%

2-Bromo-4-methylpyridine Structure

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2-Bromo-4-methy...

2-Chloro-4-picoline Structure

3678-62-4

2-Chloro-4-picoline

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2-Bromo-6-chloro-4-methylpyridine Structure

157329-89-0

2-Bromo-6-chlor...

4-Picoline Structure

108-89-4

4-Picoline

~79%

2-Chloro-4-picoline Structure

3678-62-4

2-Chloro-4-picoline

3,4-Lutidine Structure

583-58-4

3,4-Lutidine

~80%

2-BROMO-4,5-DIMETHYL-PYRIDINE Structure

66533-31-1

2-BROMO-4,5-DIM...

3,4-Lutidine Structure

583-58-4

3,4-Lutidine

~82%

2-CHLORO-4,5-DIMETHYLPYRIDINE Structure

343268-69-9

2-CHLORO-4,5-DI...


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