Home / Publications / A straightforward synthesis of 2(3),6,6-trimethyl- 6,7-dihydrobenzofuran-4(5H)-ones

A straightforward synthesis of 2(3),6,6-trimethyl- 6,7-dihydrobenzofuran-4(5H)-ones

Niftali N Yusifov 1
Niftali N Yusifov
, 
Valeh M Ismayilov 1
Valeh M Ismayilov
, 
Nurlana D Sadigova 1
Nurlana D Sadigova
, 
Maximilian N Kopylovich 2
Maximilian N Kopylovich
, 
Kamran T Mahmudov 1, 2
Kamran T Mahmudov
2 Departimento de Engenharia Química, Instituto Superior Técnico, Universidade Técnica de Lisboa, Lisboa, Portugal
10.1016/j.mencom.2013.09.019
Published 2013-09-10
Communication , Volume 23, Issue 5, 292-293
6
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Yusifov N. N. et al. A straightforward synthesis of 2(3),6,6-trimethyl- 6,7-dihydrobenzofuran-4(5H)-ones // Mendeleev Communications. 2013. Vol. 23. No. 5. pp. 292-293.
GOST all authors (up to 50) Copy
Yusifov N. N., Ismayilov V. M., Sadigova N. D., Kopylovich M. N., Mahmudov K. T. A straightforward synthesis of 2(3),6,6-trimethyl- 6,7-dihydrobenzofuran-4(5H)-ones // Mendeleev Communications. 2013. Vol. 23. No. 5. pp. 292-293.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2013.09.019
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2013.09.019
TI - A straightforward synthesis of 2(3),6,6-trimethyl- 6,7-dihydrobenzofuran-4(5H)-ones
T2 - Mendeleev Communications
AU - Yusifov, Niftali N
AU - Ismayilov, Valeh M
AU - Sadigova, Nurlana D
AU - Kopylovich, Maximilian N
AU - Mahmudov, Kamran T
PY - 2013
DA - 2013/09/10
PB - Mendeleev Communications
SP - 292-293
IS - 5
VL - 23
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2013_Yusifov,
author = {Niftali N Yusifov and Valeh M Ismayilov and Nurlana D Sadigova and Maximilian N Kopylovich and Kamran T Mahmudov},
title = {A straightforward synthesis of 2(3),6,6-trimethyl- 6,7-dihydrobenzofuran-4(5H)-ones},
journal = {Mendeleev Communications},
year = {2013},
volume = {23},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2013.09.019},
number = {5},
pages = {292--293},
doi = {10.1016/j.mencom.2013.09.019}
}
MLA
Cite this
MLA Copy
Yusifov, Niftali N., et al. “A straightforward synthesis of 2(3),6,6-trimethyl- 6,7-dihydrobenzofuran-4(5H)-ones.” Mendeleev Communications, vol. 23, no. 5, Sep. 2013, pp. 292-293. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2013.09.019.

Abstract

Alkylation of dimedone with 1,2,3-trichloro- or 1,2,3-tribromopropanes in the presence of K2CO3 in DMSO follows both O- and C-alkylation pathways giving 3-(2-haloprop-2-enyloxy)-5,5-dimethylcyclohex-2-enone and 2-(2-haloprop-2-enyl)-3-hydroxy-5,5-di- methylcyclohex-2-enone. These compounds on heating afford 3,6,6-trimethyl- and 2,6,6-trimethyl-6,7-dihydrobenzofuran-4(5H)-ones, respectively.

References

2.
Alkylation of sterically hindered 1,3-diketones under phase-transfer conditions
Zanina A.S., Shergina S.I., Sokolov I.E., Shvartsberg M.S.
Russian Chemical Bulletin, 1996
3.
Electroorganic chemistry. 103. Selective C-alkylation of .beta.-diketones
Shono T., Kashimura S., Sawamura M., Soejima T.
Journal of Organic Chemistry, 1988
6.
Alkylation of?-diketones of the hexahydroindan series and their enamines
Ivanova L.N., Severina T.A., Kogan G.A., Kucherov V.F.
Russian Chemical Bulletin, 1966
7.
Alkylation of Cyclic 1,3-Diketones
Rajamannar T., Palani N., Balasubramanian K.K.
Synthetic Communications, 1993
8.
Synthesis and structure–activity relationships of a series of substituted 2-(1H-furo[2,3-g]indazol-1-yl)ethylamine derivatives as 5-HT2C receptor agonists
Shimada I., Maeno K., Kazuta K., Kubota H., Kimizuka T., Kimura Y., Hatanaka K., Naitou Y., Wanibuchi F., Sakamoto S.
Bioorganic and Medicinal Chemistry, 2008
10.
Synthesis of 3-Substituted Pentane-2,4-Diones: Valuable Intermediates For Liquid Crystals
Cativiela C., Serrano J.L., Zurbano M.M.
Journal of Organic Chemistry, 1995
11.
SYNTHESIS OF OXYGEN HETEROCYCLES FROM 2-ARYLIDENE-1,3-D1 KETONES
Ciller J.A., Martín N., Quinteiro M., Seoane C., Soto J.L.
Organic Preparations and Procedures International, 1986
12.
Oxygen-atom transfer reagents: New, reactive α-azohydroperoxides
Baumstark A.L., Dotrong M., Vasquez P.C.
Tetrahedron Letters, 1987
13.
The Alkylation of Cyclic Diketone Thallium(I) Salts
McIntosh J.M., Beaumier P.M.
Canadian Journal of Chemistry, 1973
14.
Alkylation of β-dicarbonyl compounds with 1,2-dibromocyclohexane
Sadykhov N.S., Nasibov S.S., Muradova F.M., Gasymov R.A.
Russian Chemical Bulletin, 1998
15.
10.1016/j.mencom.2013.09.019_bib0075
Zefirov
Russ. J. Org. Chem., 1983
16.
10.1016/j.mencom.2013.09.019_bib0080
Zefirov
Russ. J. Org. Chem., 1983
17.
Alkylation of ?-dicarbonyl compounds by 1,2,3-trihalopropanes as a method for the preparation of ?-substituted furans
Akhmedov S.T., Sadykhov N.S., Ismailov V.M., Akhundova M.A., Sadovaya N.K., Karimov F.N., Zefirov N.S.
Chemistry of Heterocyclic Compounds, 1986
18.
10.1016/j.mencom.2013.09.019_bib0090
Akhmedov
J. Heterocycl. Chem., 1984
23.
Heterocyclization reaction of propargyl acetate with β-dicarbonyl compounds
Badanyan S.O., Chobanyan Z.A., Tirakyan M.R., Danielyan A.O.
Chemistry of Heterocyclic Compounds, 1998
26.
Freelingyne, an acetylenic sesquiterpenoid
Massy-Westropp R.A., Reynolds G.D., Spotswood T.M.
Tetrahedron Letters, 1966
28.
Total synthesis of (.+-.)-gnididione and (.+-.)-isognididione
Jacobi P.A., Selnick H.G.
Journal of Organic Chemistry, 1990
29.
Cytotoxic and aromatic constituents from Salvia miltiorrhiza
DON M., SHEN C., SYU W., DING Y., SUN C.
Phytochemistry, 2006
33.
REGIOSPECIFIC ALKYLATION OF CYCLOHEXENONES. A REVIEW
Podraza K.F.
Organic Preparations and Procedures International, 1991