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

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10.3762-bjoc.13.83.pdf

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2017-5-4

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Yenice, Işıl
Basceken, Sinan
Balci, Metin

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Intramolecular nucleophilic and electrophilic cyclization of N-alkyne-substituted pyrrole esters is described. Efficient routes towards the synthesis of pyrrolopyrazinone, pyrrolotriazinone and pyrrolooxazinone have been developed. First, N-alkyne-substituted pyrrole ester derivatives were synthesized. Introduction of various substituents into the alkyne functionality was accomplished by a copper-catalyzed cross-coupling reaction. Nucleophilic cyclization of N-alkyne-substituted methyl 1H-pyrrole-2carboxylates with hydrazine afforded the 6-exo-dig/6-endo-dig cyclization products depending on the electronic nature of the substituents attached to the alkyne. On the other hand, cyclization of N-alkyne-substituted methyl 1H-pyrrole-2-carboxylates with iodine only resulted in the formation of the 6-endo-dig cyclization product regardless of the substitution of the alkyne functionality.

Subject Keywords

Alkyne cyclization, Pyrrole, Pyrrolooxazinone, Pyrrolopyrazinone, Pyrrolotriazinone

URI

https://hdl.handle.net/11511/51584

Journal

Beilstein Journal of Organic Chemistry

DOI

https://doi.org/10.3762/bjoc.13.83

Collections

Department of Chemistry, Article

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Citation Formats

I. Yenice, S. Basceken, and M. Balci, “Nucleophilic and electrophilic cyclization of N-alkyne-substituted pyrrole derivatives: Synthesis of pyrrolopyrazinone, pyrrolotriazinone, and pyrrolooxazinone moieties,” Beilstein Journal of Organic Chemistry, pp. 825–834, 2017, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/51584.