The behavior of dimethylamino-substituted 2,5-diaryloxazoles and 2,5-diaryl-1,3,4-oxadiazoles under Vilsmeier-Haack conditions

L. D. Patsenker; I. G. Ermolenko; O. N. Lyubenko; I. A. Fedyunyaeva; N. A. Popova; O. S. Galkina; A. V. Mazepa; B. M. Krasovitskii

doi:10.1023/A:1024777700217

The behavior of dimethylamino-substituted 2,5-diaryloxazoles and 2,5-diaryl-1,3,4-oxadiazoles under Vilsmeier-Haack conditions

L. D. Patsenker
, I. G. Ermolenko
, O. N. Lyubenko
, I. A. Fedyunyaeva
, N. A. Popova
, O. S. Galkina
, A. V. Mazepa
, B. M. Krasovitskii

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

1 Scopus citations

Abstract

It has been shown that dimethylamino-substituted 2,5-diaryloxazoles and 2,5-diaryl-1,3,4-oxadiazoles undergo heterocyclization under Vilsmeier-Haack conditions with the participation of the dimethylamino group to form quinazolinium salts. The oxazole ring can also be formylated at the free 4 position. In alkaline medium the quinazolinium ring is readily hydrolyzed with desalkylation.

Original language	English
Pages (from-to)	525-533
Number of pages	9
Journal	Chemistry of Heterocyclic Compounds
Volume	39
Issue number	4
DOIs	https://doi.org/10.1023/A:1024777700217
State	Published - Apr 2003
Externally published	Yes

Keywords

2,5-diaryl-1,3,4-oxadiazoles
2,5-diaryloxazoles
Dimethylamino-substituted
Heterocyclization
Hydrolysis
Quinazolinium salts
Vilsmeier reaction

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10.1023/A:1024777700217

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@article{e46dce3ea41748f6afe67b6161d1c372,

title = "The behavior of dimethylamino-substituted 2,5-diaryloxazoles and 2,5-diaryl-1,3,4-oxadiazoles under Vilsmeier-Haack conditions",

abstract = "It has been shown that dimethylamino-substituted 2,5-diaryloxazoles and 2,5-diaryl-1,3,4-oxadiazoles undergo heterocyclization under Vilsmeier-Haack conditions with the participation of the dimethylamino group to form quinazolinium salts. The oxazole ring can also be formylated at the free 4 position. In alkaline medium the quinazolinium ring is readily hydrolyzed with desalkylation.",

keywords = "2,5-diaryl-1,3,4-oxadiazoles, 2,5-diaryloxazoles, Dimethylamino-substituted, Heterocyclization, Hydrolysis, Quinazolinium salts, Vilsmeier reaction",

author = "Patsenker, \{L. D.\} and Ermolenko, \{I. G.\} and Lyubenko, \{O. N.\} and Fedyunyaeva, \{I. A.\} and Popova, \{N. A.\} and Galkina, \{O. S.\} and Mazepa, \{A. V.\} and Krasovitskii, \{B. M.\}",

note = "Funding Information: The authors express their gratitude to chemical sciences candidate S. V. Iksanova (Institute of Organic Chemistry, Ukraine National Academy of Sciences, Kiev) for measurement of the 1H NMR spectra. The work was carried out with the support of the Ukraine National Academy of Sciences (grant No. 0801051062).",

year = "2003",

month = apr,

doi = "10.1023/A:1024777700217",

language = "אנגלית",

volume = "39",

pages = "525--533",

journal = "Chemistry of Heterocyclic Compounds",

issn = "0009-3122",

publisher = "Springer",

number = "4",

}

TY - JOUR

T1 - The behavior of dimethylamino-substituted 2,5-diaryloxazoles and 2,5-diaryl-1,3,4-oxadiazoles under Vilsmeier-Haack conditions

AU - Patsenker, L. D.

AU - Ermolenko, I. G.

AU - Lyubenko, O. N.

AU - Fedyunyaeva, I. A.

AU - Popova, N. A.

AU - Galkina, O. S.

AU - Mazepa, A. V.

AU - Krasovitskii, B. M.

N1 - Funding Information: The authors express their gratitude to chemical sciences candidate S. V. Iksanova (Institute of Organic Chemistry, Ukraine National Academy of Sciences, Kiev) for measurement of the 1H NMR spectra. The work was carried out with the support of the Ukraine National Academy of Sciences (grant No. 0801051062).

PY - 2003/4

Y1 - 2003/4

N2 - It has been shown that dimethylamino-substituted 2,5-diaryloxazoles and 2,5-diaryl-1,3,4-oxadiazoles undergo heterocyclization under Vilsmeier-Haack conditions with the participation of the dimethylamino group to form quinazolinium salts. The oxazole ring can also be formylated at the free 4 position. In alkaline medium the quinazolinium ring is readily hydrolyzed with desalkylation.

AB - It has been shown that dimethylamino-substituted 2,5-diaryloxazoles and 2,5-diaryl-1,3,4-oxadiazoles undergo heterocyclization under Vilsmeier-Haack conditions with the participation of the dimethylamino group to form quinazolinium salts. The oxazole ring can also be formylated at the free 4 position. In alkaline medium the quinazolinium ring is readily hydrolyzed with desalkylation.

KW - 2,5-diaryl-1,3,4-oxadiazoles

KW - 2,5-diaryloxazoles

KW - Dimethylamino-substituted

KW - Heterocyclization

KW - Hydrolysis

KW - Quinazolinium salts

KW - Vilsmeier reaction

UR - https://www.scopus.com/pages/publications/0142060099

U2 - 10.1023/A:1024777700217

DO - 10.1023/A:1024777700217

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AN - SCOPUS:0142060099

SN - 0009-3122

VL - 39

SP - 525

EP - 533

JO - Chemistry of Heterocyclic Compounds

JF - Chemistry of Heterocyclic Compounds

IS - 4

ER -

The behavior of dimethylamino-substituted 2,5-diaryloxazoles and 2,5-diaryl-1,3,4-oxadiazoles under Vilsmeier-Haack conditions

Abstract

Keywords

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