ChemInform Abstract: A Novel Route to Isoalloxazines Using 1‐Alkyl‐2‐amino‐1,5,6,7‐tetrahydroquinoxaline‐3‐carbonitriles (or Methyl Carboxylates).

Lacroix, Alain; Schabat, D.; Clerin, Daniel; Fleury, J.‐P.

doi:10.1002/chin.198819208

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Copper-mediated Flavin 3-n-arylation1

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2008

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“…The application of boronic acid esters 9 and 10 ( Figure 2), instead of boronic acids 2-R, gave ambivalent results (entries [18][19][20]. Under standard reaction conditions, with ethylene ester 9 a yield of 19% of the product (25% corrected by conversion, 23% recovered flavin 1a) was achieved.…”

Section: Copper-mediated Flavin 3-n-arylationmentioning

confidence: 84%

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Copper-Mediated 3-N-Arylation of Flavins

Attenberger¹,

Schmaderer²,

König³

2008

Synthesis

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A generally applicable method for the direct 3-N-arylation of flavins using arylboronic acids and copper acetate was developed. The reaction conditions were optimized considering the lability of flavins in basic conditions and thermal heating. Donorand acceptor-substituted arylboronic acids were used yielding 3-Narylflavins in moderate to good yields by C(aryl)-N(imide) bond formation. UV and fluorescence measurements indicate an orthogonal orientation of the additional aromatic substituent to the flavin ring system. The arene substituent is not electronically coupled to the flavin p-system in the ground state, but electron-rich arene substituents in 3-N position significantly reduce the flavin emission intensity.

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Section: Copper-mediated Flavin 3-n-arylationmentioning

confidence: 84%

“…11d, [15][16] So far, only few examples are known with aryl substitution at the 3-N position. [17][18][19][20][21][22] However, introduction of these aryl substituents requires additional steps before the flavin ring system is cyclized. Direct arylation of flavins at this position may provide a short cut creating valuable flavin derivatives.…”

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confidence: 99%