Recyclization of pyrrolo[1,2-a]pyrazinium salts into 6- and 8-aminoindolizines

Теренин, В. И.; Kabanova, E. V.; Feoktistova, E. S.; Bundel, Yu. G.

doi:10.1007/bf00474489

Chem Heterocycl Compd

1992

DOI: 10.1007/bf00474489

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Recyclization of pyrrolo[1,2-a]pyrazinium salts into 6- and 8-aminoindolizines

В. И. Теренин

E. V. Kabanova

E. S. Feoktistova

et al.

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Cited by 2 publications

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“…There are a few examples of ANRORC reactions involving the 1,4-diazine ring. Some occur as nucleophilic substitution of the halogen by an amino group, such as in α-halopyrazines [1], others are enamine rearrangements of compounds in the pyrrolo[1,2-a]pyrazine series containing a methylene or methine group in the 1 position [2,3].…”

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Novel Ring Transformation of 6-Trifluoroacetylpyrrolo[1,2-a]pyrazinium Salts to Form Pyrrolo[1,2-a]pyrazinones

Теренин

Иванов

2005

Chem Heterocycl Compd

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Keywords: pyrrolo[1,2-a]pyrazine, pyrrolo[1,2-a]pyrazin-1-one, nucleophilic rearrangement. The ability of the pyrazine ring to open when treated with nucleophiles remains little studied. There are a few examples of ANRORC reactions involving the 1,4-diazine ring. Some occur as nucleophilic substitution of the halogen by an amino group, such as in α-halopyrazines [1], others are enamine rearrangements of compounds in the pyrrolo[1,2-a]pyrazine series containing a methylene or methine group in the 1 position [2, 3].We have observed an unusual ring transformation of the pyrazine ring with retention of the type of heterocyclic system. When treated with an aqueous solution of methylamine, the 1-ethyl-and 1-phenyl-6-trifluoroacetylpyrrolo[1,2-a]pyrazinium methyl iodides (1a,b) are converted to the corresponding 6-acyl-2-methylpyrrolo[1,2-a]pyrazinones 2a,b.The scheme for such a rearrangement probably includes initial attack by the nucleophile at the positions 1 or 3 of the salt 1a,b. Subsequent opening of the pyrazine ring leads to intermediate A, the enamine group of which attacks the electrophilic center of the trifluoroacetyl group. Cleavage of trifluoromethane leads to products 2a,b. N N O F 3 C R Me N O F 3 C R MeNH NMe N N O Me O R MeNH 2 1a,b A 2a,b + H 2 O -MeNH 2 , -CF 3 H I -+ 1, 2 a R = Ph; b R = EtConversion of pyrrolo[1,2-a]pyrazinium salts to pyrrolo[1,2-a]pyrazinones is an ANRORC ring transformation of a previously unknown structural type, occurring with exchange of two exocyclic carbon atoms. __________________________________________________________________________________________

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Novel Ring Transformation of 6-Trifluoroacetylpyrrolo[1,2-a]pyrazinium Salts to Form Pyrrolo[1,2-a]pyrazinones

Теренин

Иванов

2005

Chem Heterocycl Compd

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Optimisation, scope and limitations of the synthesis of 5-aminoindolizines from oxazolo[3,2-a]pyridinium salts

Tielmann

Hoenke

2006

Tetrahedron Letters

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Recyclization of pyrrolo[1,2-a]pyrazinium salts into 6- and 8-aminoindolizines

Cited by 2 publications

References 4 publications

Novel Ring Transformation of 6-Trifluoroacetylpyrrolo[1,2-a]pyrazinium Salts to Form Pyrrolo[1,2-a]pyrazinones

Novel Ring Transformation of 6-Trifluoroacetylpyrrolo[1,2-a]pyrazinium Salts to Form Pyrrolo[1,2-a]pyrazinones

Optimisation, scope and limitations of the synthesis of 5-aminoindolizines from oxazolo[3,2-a]pyridinium salts

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