Reactions of 5(4Н)-oxazolones involving organosilone reagents
- Autores: Topuzyan V.O.1, Hovannesyan A.A.1
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Afiliações:
- Institute of Fine Organic Chemistry of the Scientific and Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia
- Edição: Volume 60, Nº 5 (2024)
- Páginas: 562-604
- Seção: Articles
- URL: https://vestnikugrasu.org/0514-7492/article/view/685338
- DOI: https://doi.org/10.31857/S0514749224050025
- EDN: https://elibrary.ru/RDMGCS
- ID: 685338
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Resumo
The review summarizes, systematizes and analyzes published literature data concerning the reactions of saturated and unsaturated 5(4H)-oxazolones with various organosilicon reagents. Examples of the preparation of heterocyclic compounds, 4,4-disubstituted 5(4H)-oxazolones, α,α-disubstituted α-amino acids and their esters using these reactions are considered. For some processes, transformation mechanisms are given. Examples of the synthesis of biologically active and natural compounds based on reactions involving 5(4H)-oxazolones and organosilicon reagents are presented.
Texto integral

Sobre autores
V. Topuzyan
Institute of Fine Organic Chemistry of the Scientific and Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia
Autor responsável pela correspondência
Email: vtop@web.am
ORCID ID: 0000-0002-1721-1993
Armênia, Yerevan, ave. Azatutyan, 26
A. Hovannesyan
Institute of Fine Organic Chemistry of the Scientific and Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia
Email: vtop@web.am
ORCID ID: 0000-0003-0879-6800
Armênia, Yerevan, ave. Azatutyan, 26
Bibliografia
- Paddibhotla S., Jayakumar S., Tepe J.J. Org. Lett., 2002, 4, 3533–3535. doi: 10.1021/o1026703y
- Paddibhotla S., Tepe J.J. Synthesis, 2003, 1433–1440. doi: 10.1055/s-2003-40196.
- Sharma V., Tepe J.J. Org. Lett., 2005, 7, 5091–5094. doi: 10.1021/o1052118w
- Kahlon D.K., Lansdell T.A., Fisk J.S., Hupp C.D., Friebe T.L., Hovde S., Jones A.D., Dyer R.D., Henry R.W., Tepe J.J. J. Med. Chem., 2009, 52, 1302–1309. doi: 10.1021/jm8013162
- Kahlon D.K., Lansdell T.A., Fisk J.S., Tepe J.J. Bioorg. Med. Chem., 2009, 17, 3093–3103. doi: 10.1016/bmc.2009.03.002
- Fisk J.S., Mosey R.A., Tepe J.J. Chem. Soc .Rev., 2007, 36, 1432–1440. doi: 10.1039/B511113G
- US Patent No: US 6,878,735 B2, 04.12.2005, Tepe J.J., Lansing E., Paddibhotla S. Multi-substituted imidazolines and method of use thereof.
- Sharma V., Peddibhotla S., Tepe J.J., Chem. Biol., 2004, 11, 1689–1699. doi: 10.1016/j.chembiol.2004.10.006
- Azevedo L.M., Lansdell T.A., Ludwig J.R., Mosey R.A., Woloch D.K., Cogan D.P., Patten G.P., Kuszpit M.R., Fisk J.S., Tepe J.J. J. Med. Chem., 2013, 56, 5974–5978. doi: 10.1021/jm400235r
- Njomen E., Osmulski P.A., Jones C., Gaczynska M.E., Tepe J.J. Biochemistry, 2018, 57, 4214–4224. doi: 10.1021/acs.biochem.8b00579
- Lansdell T.A., Hurchla M.A., Xiang J., Hovde S., Weilbaecher K.N., Henry R.W., Tepe J.J. ACS Chem. Biol., 2012, 8, 578–587. doi: 10.1021/cb300568r
- Qu K., Fisk J.S., Tepe J.J. Tetrahedron Lett., 2011, 52, 4840-4842. doi: 10.1016/j.tetlet.2011.07.022
- Zhao H.-W., Liu Y.-Y., Zhao Y.-D., Pang H.-L., Chen X.-Q., Song X.-Q., Tian T., Li B. Yang Z., Du J., Feng N.-N. Org. Lett., 2017, 19, 26–29. doi: 10.1021/acs.orglett.6b03206
- Zhao H.-W., Du J., Guo J.-M., Feng N.-N., Wang L.-R., Ding W.-Q., Song X.-Q. Chem. Commun., 2018 54, 9178–9181. doi: 10.1039/c8cc04584d
- Fritschi S.P., Linden A., Heimgartner H., Helv. Chim. Acta, 2016, 99, 1–16. doi: 10.1002/hlca.201600023
- Zhao H.-W., Liu Y.-Y., Zhao Y.-D., Feng N.-N., Du J., Song X.-Q., Pang H.-L., Chen X.-Q. Eur. J. Org. Chem., 2018, 341–346. doi: 10.1002/ejoc.201701496
- Markl G., Dorfmeister G. Tetrahedron Lett., 1986, 27, 4419–4422. doi: 10.1016/S0040-4039(00)84967-9
- Markl G., Dorfmeister G. Tetrahedron Lett., 1987, 28, 1089–1092. doi: 10.1016/S0040-4039(00)95918-5
- Cabrera S., Reyes E., Aleman J., Milelli A., Kobbelgaard S., Jorgensen K.A. J. Am. Chem. Soc., 2008, 130, 12031–12037. doi: 10.1021/ja804567h
- Weber M., Jautze S., Frey W., Peters R. Chem. Eur. J., 2012, 18, 14792–14804. doi: 10.1002/chem.201202455
- Weber M, Jautze S., Frey W., Peters R. J. Am. Chem. Soc., 2010, 132, 12222–12225. doi: 10.1021/ja106088v
- Weber M., Frey W., Peters R. Adv. Synth. Catal., 2012, 354, 1443–1449. doi: 10.1002/adsc.201200085
- Hoppe D, Liebigs Ann. Chem., 1976, 2185–2193. doi: 10.1002/jlac.197619761206
- Takagaki H., Tanabe Sh., Asaoka M., Takei H. Chem. Lett., 1979, 8, 347–350. doi: 10.1246/cl.1979.347
- Hassaner A., Ficher B., Tetrahedron, 1989, 45, 3535–3546. doi: 10.1016/s0040-4020(01)81032-2
- Takagaki H., Yasuda N., Asaoka M., Takei H. Chem. Lett., 1979, 8, 183–186. doi: 10.1246/cb.1979.183
- Lott R.S., Breitholle E.G., Stammer C.H. J. Org. Chem., 1980, 45, 1151–1153. doi: 10.1021/jo01294a046
- Huang Y., Walji A.M., Larsen C.H., MacMillan D.W.C., J. Am. Chem. Soc., 2005, 127, 15051–15053. doi: 10.1021/ja055545d
- Wilde R.G. Tetrahedron Lett., 1988, 29, 2027–2030. doi: 10.1016/S0040-4039(00)87825-9
- Тrost B.M., Ariza X., J. Am. Chem. Soc., 1999, 121, 10727–10737. doi: 10.1021/ja992754n
- Trost B.M., Lee C.B. J. Am. Chem. Soc., 1998, 120, 6818–6819. doi: 10.1021/ja981141s
- Trost M.B., Lee Ch., J. Am. Chem. Soc., 2001, 123, 12191–12201. doi: 10.1021/ja0118338
- Sofia M.J., Chakravarty P.K., Katzenellenbogen J.A. J. Org. Chem., 1983, 48, 3318–3325. doi: 10.1021/jo00167a032
- Yamada K., Kurokawa T., Tokuyama H., Fukuyama T., J. Am. Chem. Soc., 2003, 125, 6630–6631. doi: 10.1021/ja035303i
- Finkbeiner P., Weckenmann N.M., Nachtsheim B.J. Org. Lett., 2014, 16, 1326–1329. doi: 10.1021/ol500053c
- Kamlar M., Cisarova I., Vesely J. Org. Biomol. Chem., 2015, 13, 2484–2489. doi: 10.1039/c4OB02625
- Yu X.-Y., Chen J.R., Wei Q., Cheng H.G., Liu Z.-Ch., Xiao W.-J. Chem. Eur. J., 2016, 22, 6774–6778. doi: 10.1002/chem.201601227
- Badiola E., Fiser B., Gomez-Bengoa E., Mielgo A., Olaizola I., Urruzuno I., Garsia J.M., Odriozola J.M.,Razkin J., Oiarbide M., Palomo C. J. Am. Chem. Soc., 2014, 136, 17869–17881. doi: 10.1021/ja510603w
- Hashimoto M., Terashima Sh. Tetrahedron Lett., 1994, 35, 9409–9412. doi: 10.1016/S0040-4039(00)78556-X
- Hashimoto M., Terashima Sh. Chem. Commun., 1998, 47, 59–64. doi: 10.3987/COM-97-S(N)2
- Hashimoto M., Matsumoto M., Terashima Sh. Tetrahedron, 2003, 59, 3041–3062. doi: 10.1016/S0040-4020(03)00378-8
- Hashimoto M., Sugiura M., Terashima Sh. Tetrahedron, 2003, 59, 3063–3087. doi: 10.1016/S0040-4020(03)00379-X
- Aleman J., Milelli A., Cabrera S., Reyes E., Jorgensen K.A. Chem. Eur. J., 2008, 14, 10958–10966. doi: 10.1002/chem.200802030
- Zhao W., Fink D.M., Labutta C.A., Radosevich A.T. Org. Lett., 2013, 15, 3090–3093. doi: 10.1021/ol401276b
- Qiao B, Liu X, Duan S., Yan L., Jiang Z., Org. Lett., 2014, 16, 672–675. doi: 10.1021/ol403303k
- Alba A-N.R., Rios R. Chem. Asi. J., 2011, 6, 720–734. doi: 10.1002/asia.201000636
- Choi Y.S., Park S., Park Y.S. Eur. J. Org. Chem., 2016, 2539–2546. doi: 10.1002/ejoc.201600201
- Dziegielewski M., Hejmanowska J., Albrecht L. Synthesis, 2014, 46, 3233–3238. doi: 10.1055/s-0034-1378997
- Weber M., Frey W., Peters R. Chem. Eur. J., 2013, 19, 8342–8351. doi: 10.1002/chem.201300224
- Streurer M., Jensen K.L., Worgull D., Jorgensen K.A. Chem Eur. J., 2012, 18, 76–79.
- doi: 10.1002/chem.201103502
- Kraus G.A., Yu F. Synthetic Communicat., 1989, 19, 2401–2407. doi: 10.1080/00397918908052640
- Topuzyan V.O., Arutyunyan L.G., Oganesyan A.A. Russ. J. Org. Chem., 2007, 43, 868–871. doi: 10.1134/S1070428007060127
- Топузян В.О., Казоян В.М., Тамазян Р.А., Айвазян А.Г., Галстян Л.Х. ЖОрХ, 2018, 54, 1355–1363. [Topuzyan V.O., Kazoyan V.M., Tamazyan R.A., Ayvazyan A.G., Galstyan L.Kh., Russ. J. Org. Chem., 2018, 54, 9, 1369–1377.] doi: 10.1134/S1070428018090178
- Топузян В.О., Казоян В.М. Докл. НАН Армении, 2018, 118, 3, 268–272.
- Топузян В.О., Оганесян А.А., Казоян В.М., Алексанян Е.Р., Докл. НАН Армении, 2019, 119, 162–170. Elib.sci.am/2019_2/09_2_2019.pdf.
- Топузян Ж.О., Оганесян А.А., Макичян А.Т., Унанян Л.С. ЖОрХ, 2022, 58, 706–717. [Topuzyan V.O., Oganesyan A.A., Makichyan A.T., Unanayan L.S. Russ. J. Org. Chem., 2022, 55, 959–967.] doi: 10.31857/S0514749222070035
- Оганесян А.А., Макичян А.Т., Алексанян Е.Р., Топузян В.О., Арм. хим. ж., 2022, 75, 203–212. doi: 10.54503/0515-9628-2022.75.2-203
- Топузян В.О., Оганесян А.А., Паносян Г.А., ЖОрХ, 2004, 40, 1692–1694. [Topuzyan V.O., Oganesyan A.A., Panosyan G.A. Russ. J. Org. Chem., 2004, 40, 1644–1646.] doi: 10.1007/s11178-005-0072-7
- Топузян В.О., Казоян В.М., Унанян Л.С., Оганесян А.А., Галстян Л.Х., Макичян А.Т. Хим. ж. Арм., 2019, 72, 159–175. arar.sci.am/dlibra/publication/206503/edition/187889/content.
- Tripathy P.K., Mukerjee A.K. Synthesis, 1985, 285–288. doi: 10.1055/s-1985-31179
- Muselli M., Colombeau L., Hedouin J., Hoarau C.H., Bischoff L. Synlett, 2016, 27, 2819–2825. doi: 10.1055/s-0035-1562524
- Collado S., Pueyo A., Baudequin Ch., Bischoff L., Jimenez A.-I., Cativiela C., Hoarau Ch., Urriolabeitia P. Eur. J. Org. Chem., 2018, 6158–6166. doi: 10.1002/ejoc.201800966
- Topuzyan V.O., Tosunyan S.R., Aleksanyan E.R., Hakobyan E.A., Hovhannisyan N.A., Makichyan A.T., Shahkhatuni A.A., Hovhannisyan A.A. Russ. J. Gen. Chem., 2023, 93, 10, 2523–2533. doi: 10.1134/S1070363223100079
- El Mkadmi M., Lazraq M., Kerbal A., Escudie J., Couret C., Ranaivonjatovo H. Phospourus, Sulfur Silicon, 1998, 134, 1, 151–169. doi: 10.1080/10426509808545459
- Furuyama T., Tang J., Wu Z.-Y., Chen J.-Z., Kobayashi N., Zhang J.-L. Inorg. Chem. Front., 2015, 2, 671–677. doi: 10.1039/C5QI00054H
- Ning Y., Jin G.-Q, Zhang J.-L. Acc. Chem. Res., 2019, 52, 2620–2633. doi: 10.1021/acs.accounts.9b00119
- Avenoza A., Busto J.H., Cativiela C., Peregrina J.M. Tetrahedron, 1994, 50, 12989–12998. doi: 10.1016/S0040-4020(01)81218-7
- Avenoza A., Cativiela C., Busto J.H., Peregrina J,M. Tetrahedron Lett., 1995, 36, 7123–7126. doi: 10.1016/S0040-4039(95)01414-D
- Ortuno R.M., Ibarzo J. Alvarez-Larena A., Piniella J.F. Tetrahedron Lett., 1996, 37, 4059–4062. doi: 10.1016/S0040-4039(96)00732-0
- Ortanо R.M., Ibarzo J.,d`Angelo J., Dumas F., Alverez-Larena A., Piniella J.F. Tetrahedron Asymm.,1996, 7, 127–138. doi: 10.1016/0957-4166(95)00429-7
- Avenoza A., Busto J.H., Paris M., Peregrina J.M., Cativiela C. J. Heterocycl. Chem., 1997, 34, 1099–1110. doi: 10.1002/jhet.5570340402
- Rodriguez-Garcia C., Ibarzo J., Alverez-Larena A., Branchadell V., Oliva A., Ortuno M. Tetrahedron, 2001, 57, 1025–1034. doi: 10.1016/S0040-4020(00)01061-9
- AvenozaA., Busto J.H., Cataviela C., Peregrina J.M. Synthesis, 1998, 1335–1338. doi: 10.1015/s-1998-6096
- Gil A.M., Buñuel E., Cativiela C., Arkivoc, 2005, (ix) 90–103. doi: 10.3998/ark.5550190.0006.910
- Izumi S.,Kobayashi Y., Takemoto Y. Org. Lett., 2016, 18, 696–699. doi: 10.1021/acs.orglett.5b03666.
- Yan J., Chen M., Sung H. H-Y., Williams I. D., Sun J. Chem. Asian J., 2018, 13, 2440–2444. doi: 10.1002/asia.201800569
- Jiang J., Qing J., Gong L.-Z. Chem. Eur. J., 2009, 15, 7031–7034. doi: 10.1002/chem.200900814
- Uraguchi D., Asai Y., Ooi T. Angew. Chem. Int. Ed., 2009, 48, 733–737. doi: 10.1002/anie.200803661
- Wang T., Yu Z., Hoon Ding Long, Phee C.Y., Lan Y., Lu Y. J. Am. Chem. Soc., 2015, 138, 265–271. doi: 10.1021/jacs.5b10524
- Hayashi Y., Obi K., Ohta Y., Okumura D., Ishikawa H. Chem. Asian J., 2009, 4, 246–249. doi: 10.1002/asia.200800394
- Dell’Amico L., Albrecht L., Naicker T., Poulsen P.H., Jorgensen K.A. J. Am. Chem. Soc., 2013, 135, 8063–8070. doi: 10.1021/ja4029928
- Jiang H., Gschwend B., Albrecht L., Hansen S.G., Jorgensen K.A. Chem. Eur. J., 2011, 17, 9032–9036. doi: 10.1002/chem.201101539
- Halskov K.S., Johansen K., Davis R.L., Steurer D.M., Jensen F., Jorgensen K.A. J. Am., Chem. Soc., 2012, 134, 12943–12946. doi: 10.1021/ja3068269
- Wang Ch-M., Xiao J-A., Wang J., Wang Sh-Sh., Deng Z-X., Yang H. J. Org. Chem., 2016, 81, 8001–8008. doi: 10.1021/acs.joc.6b01356
- Zhao Sh., Zhao Y.-Y., Lin J-B., Xie T., Liang Y-M., Xu P-F. Org.Lett., 2015, 17, 3206–3209. doi g/10.1021/acs.orglett.5b01066
- Liu X., Deng L., Jiang X., Yan W., Liu Ch., Wang R. Org. Lett., 2010, 12, 876–879. doi 10.1o21/ol902916s
- Shi Sh.-H, Huang F.-P., Zhu P., Dong Z.-W., Hui X.-P. Org. Lett., 2012, 14, 2010–2013. doi: 10.1021/ol300510b
- Melhado A.D., Luparia M., Toste F.D. J. Am. Chem. Soc., 2007, 129, 12638–12639. doi: 10.1021/ja074824t
- Melhado A.D., Amarante G.W., Wang Z.J., Luparia M., Toste F.D. J. Am. Chem. Soc., 2011, 133, 3517–3527. doi: 10.1021/ja1095045
- Martin-rodriges M., Najera C., Sansano J.M. Synlett, 2012, 23, 62–65. doi: 10.1055/s-0030-1260334
- Martin-rodriges M., Castello L.M., Najera C., Sansano J.M., Larranaga O., de Cozar A., Cossio F.P. Beilstein J. Org. Chem, 2013, 9, 2422–2433. doi: 10.3762/bjoc.9.280
- Zhu G., Yang F., Balachandran R., Hook P., Vallee R.B., Curran D.P., Day B.W. J. Med. Chem., 2006, 49, 2063–2076. doi: 10.1021/jm051030l
- Zhang Z., Sun W., Zhu G., Yang J., Zhang M., Hong L., Wang R. Chem. Commun., 2016, 52, 1377–1380. doi: 10.1039/c5cc08989a
- Sun W., Zhu G., Wu Ch., Li G., Hong L., Wang R. Angew. Chem., 2013, 125, 8795–8799. doi: 10.1002/ange.201302831
- Kawatsura M., Ikeda D., Ishii T., Komatsu Y., Uenishi J. Synlett, 2006, 2435–2438. doi: 10.1055/s-2006-950400
- Wang Ch., Luo H.-W., Gong L.-Z. Synlett, 2011, 992–994. doi: 10.1055/s-0030-1259711
- Nguyen H.V., Butler C.D., Richards Ch. J. Org. Lett., 2006 8, 769–772. doi: 10.1021/ol053050n
- Palacio C., Conno S.J. Eur. J. Org. Chem., 2013, 2013, 5398–5413. doi: 10.1002/ejoc.201300451
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