Synthesis of Pyrazines and Pyrimidines Flashcards

1
Q

synthesis symmetrical pyrazines

A

double condensation of 2-aminocarbonyls then oxidation to regain aromaticity

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2
Q

formation of 2-aminocarbonyls

A

ketone with NBS gives a-bromoketone then NaN3 gives carbonyl azide then hydrogenation to aminocarbonyl
OR
ketone with NaNO2 and HCl gives carbonyl-NO then hydrogenation to aminocarbonyl

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3
Q

synthesis of unsymmetrical pyrazines

A

diamine condensation with 1,2-dicarbonyl then oxidation to regain aromaticity

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4
Q

synthesis of pyrimidines

A

1,3-dicarbonyl and NCN fragment
OR
use 1,3-dicarbonyl fragment and use Claisen reaction
OR
DMF-DMA or orthoformates used to carbonylate ketones

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