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Intramolecular Cyclization in 4-Azido-5-ethoxycarbonyl-2-(2′-hydroxyphenyOpyrimidine: Synthesis and Properties of 3-Ethoxy-6-(2′-hydroxyphenyl)isoxazolo[3,4-d]pyrimidine

Valerii P Vetchinov 1
Valerii P Vetchinov
, 
Elena Borisovna Nikolaenkova 1
Elena Borisovna Nikolaenkova
, 
Victor Il'ich Mamatyuk 1
Victor Il'ich Mamatyuk
, 
Victor Petrovich Krivopalov 1
Victor Petrovich Krivopalov
10.1070/MC1993v003n04ABEH000263
Published 1993-08-31
Communication , Volume 3, Issue 4, 151-153
2
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Vetchinov V. P. et al. Intramolecular Cyclization in 4-Azido-5-ethoxycarbonyl-2-(2′-hydroxyphenyOpyrimidine: Synthesis and Properties of 3-Ethoxy-6-(2′-hydroxyphenyl)isoxazolo[3,4-d]pyrimidine // Mendeleev Communications. 1993. Vol. 3. No. 4. pp. 151-153.
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Vetchinov V. P., Nikolaenkova E. B., Mamatyuk V. I., Krivopalov V. P. Intramolecular Cyclization in 4-Azido-5-ethoxycarbonyl-2-(2′-hydroxyphenyOpyrimidine: Synthesis and Properties of 3-Ethoxy-6-(2′-hydroxyphenyl)isoxazolo[3,4-d]pyrimidine // Mendeleev Communications. 1993. Vol. 3. No. 4. pp. 151-153.
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TY - JOUR
DO - 10.1070/MC1993v003n04ABEH000263
UR - https://mendcomm.colab.ws/publications/10.1070/MC1993v003n04ABEH000263
TI - Intramolecular Cyclization in 4-Azido-5-ethoxycarbonyl-2-(2′-hydroxyphenyOpyrimidine: Synthesis and Properties of 3-Ethoxy-6-(2′-hydroxyphenyl)isoxazolo[3,4-d]pyrimidine
T2 - Mendeleev Communications
AU - Vetchinov, Valerii P
AU - Nikolaenkova, Elena Borisovna
AU - Mamatyuk, Victor Il'ich
AU - Krivopalov, Victor Petrovich
PY - 1993
DA - 1993/08/31
PB - Mendeleev Communications
SP - 151-153
IS - 4
VL - 3
ER -
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@article{1993_Vetchinov,
author = {Valerii P Vetchinov and Elena Borisovna Nikolaenkova and Victor Il'ich Mamatyuk and Victor Petrovich Krivopalov},
title = {Intramolecular Cyclization in 4-Azido-5-ethoxycarbonyl-2-(2′-hydroxyphenyOpyrimidine: Synthesis and Properties of 3-Ethoxy-6-(2′-hydroxyphenyl)isoxazolo[3,4-d]pyrimidine},
journal = {Mendeleev Communications},
year = {1993},
volume = {3},
publisher = {Mendeleev Communications},
month = {Aug},
url = {https://mendcomm.colab.ws/publications/10.1070/MC1993v003n04ABEH000263},
number = {4},
pages = {151--153},
doi = {10.1070/MC1993v003n04ABEH000263}
}
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Cite this
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Vetchinov, Valerii P., et al. “Intramolecular Cyclization in 4-Azido-5-ethoxycarbonyl-2-(2′-hydroxyphenyOpyrimidine: Synthesis and Properties of 3-Ethoxy-6-(2′-hydroxyphenyl)isoxazolo[3,4-d]pyrimidine.” Mendeleev Communications, vol. 3, no. 4, Aug. 1993, pp. 151-153. https://mendcomm.colab.ws/publications/10.1070/MC1993v003n04ABEH000263.

Abstract

The title azide in the solid state or in DMSO solution cyclizes thermally to isoxazolo[3,4-d]pyrimidine 2, which can either further rearrange to isoxazolone 3 or be transformed to hydroxylamine 5 or sulfoximine 7 on interaction with water or upon dilution of its DMSO solution by water, respectively; the tetrazolo tautomer 1T yields the acrylate 6.

References

1.
The Chemistry of Indoxazenes and Anthranils: 1966–1979
Smalley R.K.
Advances in Heterocyclic Chemistry, 1981
2.
10.1070/MC1993v003n04ABEH000263_bib1_2
Khmel’nitskii
Khimiya Furoksanov: Stroenie i Sintez (Chemistry of Furoxanes: Structure and Synthesis), 1981
3.
10.1070/MC1993v003n04ABEH000263_bib1_3
Moore
The Chemistry of Functional Groups, Supplement D, 1983
4.
10.1070/MC1993v003n04ABEH000263_bib1_4
Dyall
The Chemistry of Functional Groups, Supplement D, 1983
5.
10.1070/MC1993v003n04ABEH000263_bib1_5
Smith
Azides and Nitrenes: Reactivity and Utility, 1984
6.
Azides: their preparation and synthetic uses
Scriven E.F., Turnbull K.
Chemical Reviews, 1988
10.
See, e.g., pertinent references in ref. l.
12.
Chem. Abstr., Chemical Substances Index Entries—Isoxazolo[3,4(4,3)-x]heterocycles (1978–1990, 88–113).
13.
See, e.g., pertinent references in refs. l(a),(c), 6.
15.
A similar thermal rearrangement in 3-alkoxy-5-arylamino-2,1-benzisoxazole- 4,7-quinones has recently been reported.
17.
10.1070/MC1993v003n04ABEH000263_bib8_1
Ioffe
Khimiya Organicheskikh Proizvodnykh Gidrazina (Chemistry of Organic Derivatives of Hydrazine), 1979
18.
see ref. 7 and references cited therein.