全部 标题 作者
关键词 摘要

OALib Journal期刊
ISSN: 2333-9721
费用：99美元
投递稿件

查看量下载量

Synthesis of Tri- and Tetracycle Compounds via Reaction of 1,3-Decalinediones and 4-Hydroxycoumarines with 2-Acetyl-2-Cyclohexenes and Biological Testing

DOI: 10.4236/oalib.1100749, PP. 1-8

Subject Areas: Biotechnology, Organic Chemistry, Biochemistry, Biological Chemistry

Keywords: Synthesis, decalindion and coumarine derivatives, anticoagulative activity

Full-Text   Cite this paper   Add to My Lib

Abstract

2-Acetyl-5, 5-dimethyl-2-cyclohexen-l-one reacts with decalin-1,3-dions (9a, b) and 4-hydroxy- coumarins (13a, b) following the pattern of a Michael addition with the formation of tricyclic compounds (10a, b and 14a, b). In the case of unsubstituted 2-acetyl-2-cyclohexen-l-one reaction with 4-hydroxycoumarine follows pattern of a DieIs-Alder heterodiene condensation to form tetracycle (15). Dehydration of both types of adduct gives tetracyclic compounds (11a, b and 16a, b, c). Coumarine derivatives (14a, b, 15, 16c) were tested for anticoagulative activity.

Cite this paper

Pyrko, A. N. , Lyubin, G. S. and Bondarev, S. L. (2014). Synthesis of Tri- and Tetracycle Compounds via Reaction of 1,3-Decalinediones and 4-Hydroxycoumarines with 2-Acetyl-2-Cyclohexenes and Biological Testing. Open Access Library Journal, 1, e749. doi: http://dx.doi.org/10.4236/oalib.1100749.

References

[1]  Rapson, W.S. and Robinson, R. (1935) 307. Experiments on the Synthesis of Substances Related to the Sterols. Part II. A New General Method for the Synthesis of Substituted Cyclohexenones. Journal of the Chemical Society, 1935, 1285-1288.
http://dx.doi.org/10.1039/jr9350001285
[2]  Hawthorne, J.R. and Robinson, R. (1936) 175. Experiments on Synthesis of Substances Related to Sterols. Part XIII. Hydrocyclopentanophenanthrene Derivatives. Journal of the Chemical Society, 1936, 763-765.
http://dx.doi.org/10.1039/jr9360000763
[3]  Cagniant (1963) Contribution a L’etude de la Reaction de Condention des Alkanoyl-1-cyclohexene-1 Avec les α-Tetralones. Comptes Rendus Hebdomadaires des Seances de l Academie des Sciences, 256, 4674-4676.
[4]  Schaefer, M., Weber, J. and Faller, P. (1979) Stereospecific Robinson-Stork Annelation of Heteroaromatic C-dialkylamino Compounds. Synthesis, No. 2, 122-133.
http://dx.doi.org/10.1055/s-1979-28583
[5]  Jacob, G. and Cagniant, D. (1977) Synthesis of Sulfur or Oxygen Analogs of 6,7,8,12,13,14,16,17-Octahydro-12-oxo- 15H-cyclopenta[a]phenanthrene and Some Their Methylated Derivatives. Comptes Rendus Hebdomadaires des Seances de l Academie des Sciences, 284, 373-375.
[6]  Robinson, R. and Slater, S.N. (1941) 72. Experiments on Synthesis of Substances Related to Sterols. Journal of the Chemical Society, No. 7, 376-385.
http://dx.doi.org/10.1039/jr9410000376
[7]  Ashton, M.J., Bailey, A.S. and Jones, E.R.H. (1974) Microbiological Hydroxylation. Part XII. Comparative Behavior of D-Homogonane Ketones and Steroids. Journal of the Chemical Society Perkin I, No. 14, 1658-1665.
http://dx.doi.org/10.1039/p19740001658
[8]  Akhrem, A.A., Moiseenkov, A.M. and Lakhvich, F.A. (1972) Use of Some 2-Acetyl-2-cyclohexen-1-one Derivatives in the Total Synthesis of Steroids. Russian Chemical Bulletin, 21, 866-868.
http://dx.doi.org/10.1007/BF00854489
[9]  Lakhvich, F.A., Khripach, V.A., Pyrko, A.N., Antonevich, I.P., Yankova, T.V., Koroleva, E.V. and Akhrem, A.A. (1988) Reductive Cleavage of 4,5-Cycloalkanoisoxazolines. Chemistry of Heterocyclic Compounds, 24, 800-804.
http://dx.doi.org/10.1007/BF00633180
[10]  Akhrem, A.A., Lakhvich, F.A. and Pyrko, A.N. (1977) Synthesis of 2-Acetyl-5,5-dimethyl-2-cyclohexen-1-ol and 5,5- dimethyl-2-(α-hydroxyethyl)-2-cyclohexen-1-on. Journal of Organic Chemistry (Russian), 13, 2074-2078.
[11]  Akhrem, A.A., Lakhvich, F.A., Khripach, V.A. and Pyrko, A.N. (1990) 2-Acetyl-2-cycloalken-1-ols in Michael- Robinson Annelation Reactions. Journal of Organic Chemistry (Russian), 26, 1932-1938.
http://dx.doi.org/10.1002/chin.199109084
[12]  Akhrem, A.A., Lakhvich, F.A. and Pyrko, A.N. (1983) Reaction of 2-acetyl-2-cycloalken-1-ones with Cyclic β-Diketones. Journal of Organic Chemistry (Russian), 19, 2322-2328.
[13]  Ozols, Ya.Ya., Pyrko, A.N., Lakhvich, F.A., Vigante, B.A., Dubure, R.R., Dubur, G.Ya. and Akhrem, A.A. (1990) Synthesis of Decahydrophenanthridine-1,7-dione and Hexahydroisoquinol-8-one Derivatives in the Deaction of 2-acetyl-2-cyclohexene-1-ones with Conjugated Enaminocarbonyl Compounds. Chemistry of Heterocyclic Compounds, 26, 58-62.
[14]  Ozols, Ya.Ya., Pyrko, A.N., Vigante, B.A., Dubure, R.R. and Dubur, G.Ya. (1992) Synthesis of Phenyl-Substituted Derivatives of Decahydro-1,7-phenanthridinedione and Hexahydro-8-isoquinolone. Chemistry of Heterocyclic Compounds, 28, 530-534.
http://dx.doi.org/10.1007/BF00475250
[15]  Reich, H.J., Renga, J.M. and Reich, I.L. (1975) Organoselenium Chemistry. Conversion of Ketones to Enones by Selenoxide Syn Elimination. Journal of the American Chemical Society, 97, 5434-5447.
http://dx.doi.org/10.1021/ja00852a019
[16]  Liotta, D., Saindane, M., Barnum, C., Ensley, H. and Balakrishnan, P. (1981) Reactions Involving Selenium Metal as an Electrophile. 2. A General Pprocedure for the Preparation of Uunsaturated β-Dicarbonyl Compounds. Tetrahedron Letters, 22, 3043-3046.
http://dx.doi.org/10.1016/S0040-4039(01)81822-0
[17]  Oliveira-Ferrer, L., Schmidt, K. and Margaretha, P. (2001) Synthesis of Nonenolizing 2-Acylcyclohex-2-enones. Helvetica Chimica Acta, 84, 3818-3821.
http://dx.doi.org/10.1002/1522-2675(20011219)84:12<3818::AID-HLCA3818>3.0.CO;2-R
[18]  Sheng, Sh.R., Liu, X.L. and Wang, X.C. (2003) Synthesis of α,β-Unsaturated Ketones and Esters Using Polymer- Supported Selenium Bromide. Journal of the Chinese Chemical Society, 50, 279-281.
[19]  Renga, J.M. and Reich, H.J. (1988) α,β-Dehydrogenationof β-Dicarbonyl Compounds by Selenoxide Elimination: 2- Acetyl-2-cyclohexen-1-one. Organic Syntheses, 6, 23-24.
[20]  Oliveira-Ferrer, L. and Margaretha, P. (1999) Synthesis and Photoreactivity of a 2-Pivaloylcyclohex-2-enone. Journal of Chemical Research, Synopses, No. 3, 204-205.
http://dx.doi.org/10.1039/a808422j
[21]  Snider, B.B. (1980) Diels-Alder Reactions of 2-acetyl-2-cyclohexenone with Enol Ethers and Emamines. Tetrahedron Letters, 21, 1133-1136.
http://dx.doi.org/10.1016/S0040-4039(01)83932-0
[22]  Kon, G.A.R. and Qudrat-i-Khuda, M. (1926) CCCCX.—Preparation of Cis-o-carboxycyclohexaneacetic Acid. Journal of the Chemical Society, 1926, 3071-3073.
http://dx.doi.org/10.1039/jr9262903071
[23]  Shah, V., Bose, J. and Shah, R. (1960) New Synthesis of 4-Hydroxycoumarins. Journal of Organic Chemistry, 25, 677-678.
http://dx.doi.org/10.1021/jo01074a630
[24]  Tamm, Ch. and Albrecht, R. (1960) Die Enolisation von Cholestandion-(1,3) und Verwandten Cyclischen β-Dicarbonylverbindungen. Helvetica Chimica Acta, 43, 768-782.
http://dx.doi.org/10.1002/hlca.19600430320
[25]  Muhle, H. and Tamm, Ch. (1962) über cyclische β-Diketone. 3. Mitteilung. Die Methylierung von (±)-cis- und (±)-trans-Decalindion-(1,3), sowie von (±)-2-Methyl-trans-decalindion-(1,3) mit Diazomethan. Helvetica Chimica Acta, 45, 1475-1485.
http://dx.doi.org/10.1002/hlca.19620450513
[26]  Tanaka, H., Iton, J., Ikushima, H., Okamoto, M., Kawai, J. and Imanaka, H. (1980) Structure Elucidation and Synthesis of a New Anticoccidial Substance Isolated from Streptomycesauranticolor. Tetrahedron Letters, 21, 4359-4360.
http://dx.doi.org/10.1016/S0040-4039(00)77857-9
[27]  Darbarwar, M. and Sundaramurthy, V. (1982) Synthesis of Coumarins with 3:4-Fused Ring Systems and Their Physiological Activity. Synthesis, No. 5, 337-388.
http://dx.doi.org/10.1055/s-1982-29806
[28]  Sosnovskikha, V.Ya., Moshkina, V.S. and Kodessb, M.I. (2008) A Reinvestigation of the Reactions of 3-Substituted Chromones with Hydroxylamine. Unexpected Synthesis of 3-Amino-4H-chromeno[3,4-d]isoxazol-4-one and 3-(Diaminomethylene)chroman-2,4-dione. Tetrahedron Letters, 49, 6856-6859.
http://dx.doi.org/10.1016/j.tetlet.2008.09.091
[29]  Wolfbeis, O.S. (1982) Darstellung Pyronokondensierter 2-Pyridone, Cumarine und 2-Chinolone mit Hilfe derKappe- Mayer-Variante dervon Pechmann-Reaktion. Monatshefte fiir Chemie/Chemical Monthly, 113, 365-370.
http://dx.doi.org/10.1007/BF00799563
[30]  Sharanin, Yu.A., Goncharenko, M.P. and Litvinov, V.P. (1998) Reactions of Carbonyl Compounds with α,β-Unsaturated Nitriles as a Convenient Pathway to Carbo- and Heterocycles. Russian Chemical Review, 67, 393-422.
http://dx.doi.org/10.1070/RC1998v067n05ABEH000371
[31]  Caselli, A.S., Collins, D.J. and Stone, G.M. (1982) The Structure and Function of Oestrogens. III. 3,17β-Dihydroxy- 6-oxaoestra-1,3,5(10),8(9)-tetraen-7-one and Related Steroidal Coumarins. Australian Journal of Chemistry, 35, 799- 808.
http://dx.doi.org/10.1071/CH9820799

Full-Text


comments powered by Disqus

Contact Us

service@oalib.com

QQ:3279437679

WhatsApp +8615387084133

WeChat 1538708413




©2008-2020 OALib, Inc | Public user content licensed CC-BY 4.0 unless otherwise specified. OALib ISSN Online: 2333-9721 OALib ISSN Print: 2333-9705