Recyclization reactions of 1-alkylpyrimidinium salts

Ruben S. Vardanyan; Gevork G. Danagulyan; Armen D. Mkrtchyan; Victor J. Hruby

doi:10.1515/HC.2011.025

Recyclization reactions of 1-alkylpyrimidinium salts

Ruben S. Vardanyan, Gevork G. Danagulyan, Armen D. Mkrtchyan, Victor J. Hruby

Chemistry and Biochemistry

Research output: Contribution to journal › Article › peer-review

2 Scopus citations

Abstract

The reaction of 4-amino-2-benzyl-1-methyl-5-ethoxycarbonylpyrimidinium iodide ( 3 ) with alcoholic methylamine resulted in the formation of the methylimine of 2-amino-4- hydroxy-6-methylamino-5-phenylpyridine-3-carbaldehyde ( 5 ). Heating of the same pyrimidinium salt in benzylamine gave a mixture of products of two C - C recyclizations: 2-benzyl-4-benzylamino-5- carbamoylpyrimidine ( 7 ) and the benzylimine of 4-amino-2-benzyl-6- benzylaminopyrimidine- 5-carbaldehyde ( 8 ). The reaction of 2-amino-1,4-dimethyl-5- ethoxycarbonylpyrimidinium iodide ( 10 ) with KOH ethanolic solution gave a single product of C - C-recyclization: 2-amino- 5-acetyl-4-hydroxypyrimidine ( 11 ).

Original language	English (US)
Pages (from-to)	129-133
Number of pages	5
Journal	Heterocyclic Communications
Volume	17
Issue number	3-4
DOIs	https://doi.org/10.1515/HC.2011.025
State	Published - Sep 2011

Keywords

Pyrimidinium salt
Recyclization

ASJC Scopus subject areas

Organic Chemistry

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10.1515/HC.2011.025

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@article{17cc1cf448c74d9d97b58fd491da32e9,

title = "Recyclization reactions of 1-alkylpyrimidinium salts",

abstract = "The reaction of 4-amino-2-benzyl-1-methyl-5-ethoxycarbonylpyrimidinium iodide ( 3 ) with alcoholic methylamine resulted in the formation of the methylimine of 2-amino-4- hydroxy-6-methylamino-5-phenylpyridine-3-carbaldehyde ( 5 ). Heating of the same pyrimidinium salt in benzylamine gave a mixture of products of two C - C recyclizations: 2-benzyl-4-benzylamino-5- carbamoylpyrimidine ( 7 ) and the benzylimine of 4-amino-2-benzyl-6- benzylaminopyrimidine- 5-carbaldehyde ( 8 ). The reaction of 2-amino-1,4-dimethyl-5- ethoxycarbonylpyrimidinium iodide ( 10 ) with KOH ethanolic solution gave a single product of C - C-recyclization: 2-amino- 5-acetyl-4-hydroxypyrimidine ( 11 ).",

keywords = "Pyrimidinium salt, Recyclization",

author = "Vardanyan, {Ruben S.} and Danagulyan, {Gevork G.} and Mkrtchyan, {Armen D.} and Hruby, {Victor J.}",

year = "2011",

month = sep,

doi = "10.1515/HC.2011.025",

language = "English (US)",

volume = "17",

pages = "129--133",

journal = "Heterocyclic Communications",

issn = "0793-0283",

publisher = "Walter de Gruyter GmbH",

number = "3-4",

}

TY - JOUR

T1 - Recyclization reactions of 1-alkylpyrimidinium salts

AU - Vardanyan, Ruben S.

AU - Danagulyan, Gevork G.

AU - Mkrtchyan, Armen D.

AU - Hruby, Victor J.

PY - 2011/9

Y1 - 2011/9

N2 - The reaction of 4-amino-2-benzyl-1-methyl-5-ethoxycarbonylpyrimidinium iodide ( 3 ) with alcoholic methylamine resulted in the formation of the methylimine of 2-amino-4- hydroxy-6-methylamino-5-phenylpyridine-3-carbaldehyde ( 5 ). Heating of the same pyrimidinium salt in benzylamine gave a mixture of products of two C - C recyclizations: 2-benzyl-4-benzylamino-5- carbamoylpyrimidine ( 7 ) and the benzylimine of 4-amino-2-benzyl-6- benzylaminopyrimidine- 5-carbaldehyde ( 8 ). The reaction of 2-amino-1,4-dimethyl-5- ethoxycarbonylpyrimidinium iodide ( 10 ) with KOH ethanolic solution gave a single product of C - C-recyclization: 2-amino- 5-acetyl-4-hydroxypyrimidine ( 11 ).

AB - The reaction of 4-amino-2-benzyl-1-methyl-5-ethoxycarbonylpyrimidinium iodide ( 3 ) with alcoholic methylamine resulted in the formation of the methylimine of 2-amino-4- hydroxy-6-methylamino-5-phenylpyridine-3-carbaldehyde ( 5 ). Heating of the same pyrimidinium salt in benzylamine gave a mixture of products of two C - C recyclizations: 2-benzyl-4-benzylamino-5- carbamoylpyrimidine ( 7 ) and the benzylimine of 4-amino-2-benzyl-6- benzylaminopyrimidine- 5-carbaldehyde ( 8 ). The reaction of 2-amino-1,4-dimethyl-5- ethoxycarbonylpyrimidinium iodide ( 10 ) with KOH ethanolic solution gave a single product of C - C-recyclization: 2-amino- 5-acetyl-4-hydroxypyrimidine ( 11 ).

KW - Pyrimidinium salt

KW - Recyclization

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DO - 10.1515/HC.2011.025

M3 - Article

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SN - 0793-0283

VL - 17

SP - 129

EP - 133

JO - Heterocyclic Communications

JF - Heterocyclic Communications

IS - 3-4

ER -

Recyclization reactions of 1-alkylpyrimidinium salts

Abstract

Keywords

ASJC Scopus subject areas

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