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Heterocyclization of N-[2-(cyclopent-1-enyl)phenyl]acetamides and ethyl N-[2-(cyclopent-1-enyl)phenyl]carbamates under the action of hydrogen peroxide

Rail Rafkatovich Gataullin 1
Rail Rafkatovich Gataullin
, 
Marat Faritovich Nasyrov 1
Marat Faritovich Nasyrov
, 
Olga Vladimirovna Shitikova 1
Olga Vladimirovna Shitikova
, 
Leonid Vasilevich Spirikhin 1
Leonid Vasilevich Spirikhin
, 
Ildus Barievich Abdrakhmanov 1
Ildus Barievich Abdrakhmanov
10.1070/MC2001v011n05ABEH001489
Published 2001-10-23
Communication , Volume 11, Issue 5, 200-201
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Gataullin R. R. et al. Heterocyclization of N-[2-(cyclopent-1-enyl)phenyl]acetamides and ethyl N-[2-(cyclopent-1-enyl)phenyl]carbamates under the action of hydrogen peroxide // Mendeleev Communications. 2001. Vol. 11. No. 5. pp. 200-201.
GOST all authors (up to 50) Copy
Gataullin R. R., Nasyrov M. F., Shitikova O. V., Spirikhin L. V., Abdrakhmanov I. B. Heterocyclization of N-[2-(cyclopent-1-enyl)phenyl]acetamides and ethyl N-[2-(cyclopent-1-enyl)phenyl]carbamates under the action of hydrogen peroxide // Mendeleev Communications. 2001. Vol. 11. No. 5. pp. 200-201.
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TY - JOUR
DO - 10.1070/MC2001v011n05ABEH001489
UR - https://mendcomm.colab.ws/publications/10.1070/MC2001v011n05ABEH001489
TI - Heterocyclization of N-[2-(cyclopent-1-enyl)phenyl]acetamides and ethyl N-[2-(cyclopent-1-enyl)phenyl]carbamates under the action of hydrogen peroxide
T2 - Mendeleev Communications
AU - Gataullin, Rail Rafkatovich
AU - Nasyrov, Marat Faritovich
AU - Shitikova, Olga Vladimirovna
AU - Spirikhin, Leonid Vasilevich
AU - Abdrakhmanov, Ildus Barievich
PY - 2001
DA - 2001/10/23
PB - Mendeleev Communications
SP - 200-201
IS - 5
VL - 11
ER -
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@article{2001_Gataullin,
author = {Rail Rafkatovich Gataullin and Marat Faritovich Nasyrov and Olga Vladimirovna Shitikova and Leonid Vasilevich Spirikhin and Ildus Barievich Abdrakhmanov},
title = {Heterocyclization of N-[2-(cyclopent-1-enyl)phenyl]acetamides and ethyl N-[2-(cyclopent-1-enyl)phenyl]carbamates under the action of hydrogen peroxide},
journal = {Mendeleev Communications},
year = {2001},
volume = {11},
publisher = {Mendeleev Communications},
month = {Oct},
url = {https://mendcomm.colab.ws/publications/10.1070/MC2001v011n05ABEH001489},
number = {5},
pages = {200--201},
doi = {10.1070/MC2001v011n05ABEH001489}
}
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Gataullin, Rail Rafkatovich, et al. “Heterocyclization of N-[2-(cyclopent-1-enyl)phenyl]acetamides and ethyl N-[2-(cyclopent-1-enyl)phenyl]carbamates under the action of hydrogen peroxide.” Mendeleev Communications, vol. 11, no. 5, Oct. 2001, pp. 200-201. https://mendcomm.colab.ws/publications/10.1070/MC2001v011n05ABEH001489.

Abstract

The oxidation of N-[2-(cyclopent-1-enyl)phenyl]acetamides and ethyl N-[6-methyl-2-(cyclopent-1-enyl)phenyl]carbamate with hydrogen peroxide in methanolic NaOH gave spiro[4H-3,1-benzoxazine-4,1′-cyclopentanes]. On the other hand, ethyl [2-(cyclopent- 1-enyl)phenyl]carbamate reacted with hydrogen peroxide in the presence of acetonitrile and NaOH to give ethyl 3a-hydroxy-2,3,3a,8b-tetrahydrocyclopenta[b]indole-4(1H)-carboxylate, which was dehydrated with polyphosphoric acid to ethyl 2,3-dihydrocyclopenta[b]indole-4(1H)-carboxylate.

References

1.
10.1070/MC2001v011n05ABEH001489_bib1
Gütschow
Sci. Pharm., 1999
2.
Practical Asymmetric Synthesis of Efavirenz (DMP 266), an HIV-1 Reverse Transcriptase Inhibitor
Pierce M.E., Parsons R.L., Radesca L.A., Lo Y.S., Silverman S., Moore J.R., Islam Q., Choudhury A., Fortunak J.M., Nguyen D., Luo C., Morgan S.J., Davis W.P., Confalone P.N., Chen C., et. al.
Journal of Organic Chemistry, 1998
3.
10.1070/MC2001v011n05ABEH001489_bib3
Gataullin
Izv. Akad. Nauk. Ser. Khim., 1999
4.
10.1070/MC2001v011n05ABEH001489_bib4
Gataullin
Izv. Akad. Nauk. Ser. Khim., 2000
5.
10.1070/MC2001v011n05ABEH001489_bib5
Prilezhaeva
Reaktsiya Prilezhaeva. Elektrofil’noe okislenie, 1974
6.
10.1070/MC2001v011n05ABEH001489_bib6
Gataullin
Izv. Akad. Nauk, Ser. Khim., 2000