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1 article(s) from Yenice, Işıl

Nucleophilic and electrophilic cyclization of N-alkyne-substituted pyrrole derivatives: Synthesis of pyrrolopyrazinone, pyrrolotriazinone, and pyrrolooxazinone moieties

Işıl Yenice,
Sinan Basceken and
Metin Balci

Beilstein J. Org. Chem. 2017, 13, 825–834, doi:10.3762/bjoc.13.83

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Graphical Abstract

Figure 1: Structures of some natural products containing pyrazinone and aminotriazonone skeletons.

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Figure 2: Structures of some natural products containing a pyrrolopyrazinone moiety.

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Figure 3: N-alkyne substituted pyrrole esters 7a–d.

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Scheme 1: Synthesis of N-alkyne substituted methyl 1H-pyrrole-2-carboxylate derivatives 7a–d.

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Scheme 2: Nucleophilic cyclization reaction of compounds 7a–d and acetylation of 12c.

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Figure 4: Correlations of olefinic proton in 12c and methylene protons in 13c and 16 with the relevant carbon...

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Figure 5: Single-crystal X-ray structure of 12c shown with 40% probability displacement ellipsoids.

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Scheme 3: Synthesis of 16.

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Figure 6: The structure of allene 17 formed during the reaction of 7d with a base.

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Scheme 4: Proposed reaction mechanism of nucleophilic cyclization reaction of 7.

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Scheme 5: Electrophilic cyclization reactions of 19a–c with iodine.

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Figure 7: Single-crystal X-ray structure of 19c shown with 40% probability displacement ellipsoids.

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Scheme 6: Proposed reaction mechanism of electrophilic cyclization reaction of 7c.

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Figure 8: Potential energy proﬁle related to the formation of pyrrolooxazinone 19c in the polarizable continu...

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Published 04 May 2017

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