Abstract
This review is focused on one of the most important classes of Meldrum's acid derivatives commonly known as acyl Meldrum's acids. The preparation methods of these compounds are considered including the recently proposed and rather rarely used ones. The chemical properties of acyl Meldrum's acids are described in detail, including thermal stability and reactions with various nucleiophiles. The possible mechanisms of these transformations are analyzed.
Bibliography --- 134 references.
References
1.
Meldrum A.N.
Journal of the Chemical Society Transactions ,
1908
2.
Byun K., Mo Y., Gao J.
Journal of the American Chemical Society ,
2001
3.
Arnett E.M., Harrelson J.A.
Journal of the American Chemical Society ,
1987
4.
Davidson D., Bernhard S.A.
Journal of the American Chemical Society ,
1948
5.
Pfluger C.E., Boyle P.D.
Journal of the Chemical Society Perkin Transactions 2 ,
1985
6.
6
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1953
7.
K�berl D., Schuster P.
Monatshefte fur Chemie ,
1972
8.
9.
10.
Lipson V.V., Gorobets N.Y.
Molecular Diversity ,
2009
11.
12.
Ivanov A.S.
Chemical Society Reviews ,
2008
13.
Gerencsér J., Dormán G., Darvas F.
QSAR & Combinatorial Science ,
2006
14.
Simon C., Constantieux T., Rodriguez J.
European Journal of Organic Chemistry ,
2004
15.
Yavari I., Sabbaghan M., Hossaini Z.
Molecular Diversity ,
2006
16.
Dumas A.M., Fillion E.
Accounts of Chemical Research ,
2009
17.
17
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1958
18.
Gaber A.E., McNab H.
Synthesis ,
2001
19.
Cantillo D., Sheibani H., Kappe C.O.
Journal of Organic Chemistry ,
2012
20.
Basheer A., Rappoport Z.
Journal of Physical Organic Chemistry ,
2008
21.
Lei Y.X., Casarini D., Cerioni G., Rappoport Z.
Journal of Physical Organic Chemistry ,
2003
22.
Mukhopadhyaya J.K., Sklenák S., Rappoport Z.
Journal of the American Chemical Society ,
2000
23.
Wentrup C., Rao V.V., Frank W., Fulloon B.E., Moloney D.W., Mosandl T.
Journal of Organic Chemistry ,
1999
24.
Oikawa Y., Sugano K., Yonemitsu O.
Journal of Organic Chemistry ,
1978
25.
Maibaum J., Rich D.H.
Journal of Medicinal Chemistry ,
1989
26.
M. Joullié M., R. Ewing W.
Heterocycles ,
1988
27.
Hamada Y., Kondo Y., Shibata M., Shioiri T.
Journal of the American Chemical Society ,
1989
28.
Raillard S.P., Chen W., Sullivan E., Bajjalieh W., Bhandari A., Baer T.A.
Journal of Combinatorial Chemistry ,
2002
29.
Sørensen U.S., Falch E., Krogsgaard-Larsen P.
Journal of Organic Chemistry ,
2000
30.
Emtenäs H., Alderin L., Almqvist F.
Journal of Organic Chemistry ,
2001
31.
McInnis C.E., Blackwell H.E.
Bioorganic and Medicinal Chemistry ,
2011
32.
Ley S.V., Woodward P.R.
Tetrahedron Letters ,
1987
33.
YAMAMOTO Y., WATANABE Y., OHNISHI S.
Chemical and Pharmaceutical Bulletin ,
2011
34.
Henning H., Stemplinger G., Rothe K.
1992
35.
Mahulikar P.P., Mane R.B.
Synthetic Communications ,
2005
36.
Birch M., Challenger S., Crochard J., Fradet D., Jackman H., Luan A., Madigan E., Mathew J.S., McDowall N., Meldrum K., Gordon C.M., Peach P., Yeo S.
Organic Process Research and Development ,
2011
37.
Ahn J.H., Shin M.S., Jun M.A., Jung S.H., Kang S.K., Kim K.R., Rhee S.D., Kang N.S., Kim S.Y., Sohn S., Kim S.G., Jin M.S., Lee J.O., Cheon H.G., Kim S.S., et. al.
Bioorganic and Medicinal Chemistry Letters ,
2007
38.
Xu F., Armstrong J.D., Zhou G.X., Simmons B., Hughes D., Ge Z., Grabowski E.J.
Journal of the American Chemical Society ,
2004
39.
Alker D., Campbell S.F., Cross P.E., Burges R.A., Carter A.J., Gardiner D.G.
Journal of Medicinal Chemistry ,
1989
40.
40
A. A. Krasnovskii
Biofizika ,
1960
41.
Sifferlen T., Boss C., Cottreel E., Koberstein R., Gude M., Aissaoui H., Weller T., Gatfield J., Brisbare-Roch C., Jenck F.
Bioorganic and Medicinal Chemistry Letters ,
2010
42.
Tamarez M.M., Franck R.W., Geer A.
Tetrahedron ,
2003
43.
Häusler J.
Monatshefte fur Chemie ,
1982
44.
Augstin M., G�nther E.
Monatshefte fur Chemie ,
1990
45.
Janikowska K., Makowiec S.
Synthetic Communications ,
2011
46.
46
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1955
47.
Lee H., Lee J., Lee G., Pak C.
Synlett ,
1996
48.
Janikowska K., Makowiec S., Rachoń J.
Helvetica Chimica Acta ,
2012
49.
Huang X., Chen B.
Synthesis ,
1986
50.
Bernasconi C.F., Brown S.D., Ali M., Rappoport Z., Yamataka H., Salim H.
Journal of Organic Chemistry ,
2006
51.
Huang X., Chen B.
Synthesis ,
1987
52.
Huang Z., Shi X.
Synthetic Communications ,
1990
53.
53
D. Porretand E. Rabinowitch
Nature ,
1937
54.
Fulloon B.E., Wentrup C.
Journal of Organic Chemistry ,
1996
55.
Bibas H., Moloney D.W., Neumann R., Shtaiwi M., Bernhardt P.V., Wentrup C.
Journal of Organic Chemistry ,
2002
56.
Rafai Far A.
Angewandte Chemie - International Edition ,
2003
57.
Wentrup C., Heilmayer W., Kollenz G.
Synthesis ,
1994
58.
Gudipati I.R., Sadasivam D.V., Birney D.M.
Green Chemistry ,
2008
59.
Clemens R.J., Hyatt J.A.
Journal of Organic Chemistry ,
1985
60.
Kappe C.O., Wong M.W., Wentrup C.
Journal of Organic Chemistry ,
1995
61.
Zuhse R.H., Wong M.W., Wentrup C.
The Journal of Physical Chemistry ,
1996
62.
10.1021/jo026275+
63.
YAMAMOTO Y., WATANABE Y.
Chemical and Pharmaceutical Bulletin ,
2011
64.
Sellstedt M., Almqvist F.
Organic Letters ,
2008
65.
65
A. A. Krasnovskii
Biofizika ,
1959
66.
Katagiri N., Okada M., Kaneko C., Furuya T.
Tetrahedron Letters ,
1996
67.
Katagiri N., Sato H., Kurimoto A., Okada M., Yamada A., Kaneko C.
Journal of Organic Chemistry ,
1994
68.
68
N. N. Mel'nikov
Zhur. Obshch. Khim. ,
1946
69.
Renslo A.R., Danheiser R.L.
Journal of Organic Chemistry ,
1998
70.
Cantín Á., Moya P., Miranda M.A., Primo J., Primo-Yúfera E.
Journal of Agricultural and Food Chemistry ,
1998
71.
Morita Y., Kamakura R., Takeda M., Yamamoto Y.
Chemical Communications ,
1997
72.
McGlacken G.P., McSweeney C.M., O’Brien T., Lawrence S.E., Elcoate C.J., Reen F.J., O’Gara F.
Tetrahedron Letters ,
2010
73.
Yuste F., Breña F.K., Barrios H., Sánchez-Obregón R., Ortíz B., Walls F.
Synthetic Communications ,
1988
74.
Punda P., Makowiec S.
Synthetic Communications ,
2013
75.
Pak C.S., Yang H.C., Choi E.B.
Synthesis ,
1992
76.
Cassis R., Tapia R., Valderrama J.A.
Synthetic Communications ,
1985
77.
Nobes R.H., Bouma W.J., Radom L.
Journal of the American Chemical Society ,
1983
78.
Zawacki F.J., Crimmins M.T.
Tetrahedron Letters ,
1996
79.
Janikowska K., Makowiec S., Rachoń J.
Helvetica Chimica Acta ,
2013
80.
Basheer A., Rappoport Z.
Journal of Organic Chemistry ,
2007
81.
Augustin M., Günther E.
Zeitschrift für Chemie ,
2010
82.
Hase T.A., Salonen K.
Synthetic Communications ,
1980
83.
Fritz H., Lehmann J., Schlesselmann P.
Carbohydrate Research ,
1983
84.
84
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1947
85.
86.
Rogers H.R., McDermott J.X., Whitesides G.M.
Journal of Organic Chemistry ,
1975
87.
Thomas R.J., Campbell K.N., Hennion G.F.
Journal of the American Chemical Society ,
1938
88.
Rosowsky A., Forsch R., Uren J., Wick M., Kumar A.A., Freisheim J.H.
Journal of Medicinal Chemistry ,
1983
89.
Akué-Gédu R., El-Hafidi H., Rigo B., Couturier D.
Journal of Heterocyclic Chemistry ,
2006
90.
Obaza J., Smith F.X.
Synthetic Communications ,
1982
91.
Haulotte E., Laurent P., Braekman J.
European Journal of Organic Chemistry ,
2012
92.
Facile stereoselective synthesis of ?-substituted ?-amino acids from the corresponding ?-amino acids
Smrcina M., Majer P., Majerová E., Guerassina T.A., Eissenstat M.A.
Tetrahedron ,
1997
93.
Casimir J.R., Didierjean C., Aubry A., Rodriguez M., Briand J., Guichard G.
Organic Letters ,
2000
94.
Kim H., Kim M., Lee J., Yu H., Hah J.
Bioorganic and Medicinal Chemistry ,
2011
95.
Tietze L.F., Steinmetz A., Balkenhohl F.
Bioorganic and Medicinal Chemistry Letters ,
1997
96.
97.
Häusler J.
European Journal of Organic Chemistry ,
1983
98.
Lermer L., Neeland E.G., Ounsworth J.P., Sims R.J., Tischler S.A., Weiler L.
Canadian Journal of Chemistry ,
1992
99.
Kang J., Kim Y.H., Park M., Lee C.H., Kim W.
Synthetic Communications ,
1984
100.
Lokot I.P., Pashkovsky F.S., Lakhvich F.A.
Tetrahedron ,
1999
101.
Organic Syntheses ,
1985
102.
YAMAMOTO Y., OHNISHI S., AZUMA Y.
Chemical and Pharmaceutical Bulletin ,
2011
103.
Huggins M.T., Barber P.S., Florian D., Howton W.
Synthetic Communications ,
2008
104.
Oikawa Y., Mohri K., Hirao K., Yonemitsu O.
Heterocycles ,
1982
105.
Jouin P., Castro B., Nisato D.
Journal of the Chemical Society Perkin Transactions 1 ,
1987
106.
Wittenberger S.J., Baker W.R., Donner B.G., Hutchins C.W.
Tetrahedron Letters ,
1991
107.
Altmann K., Freier S.M., Pieles U., Winkler T.
1994
108.
Jiang J., Li W., Przeslawski R.M., Joullié M.M.
Tetrahedron Letters ,
1993
109.
Fehrentz J., Bourdel E., Califano J., Chaloin O., Devin C., Garrouste P., Lima-Leite A., Llinares M., Rieunier F., Vizavonna J., Winternitz F., Loffet A., Martinez J.
Tetrahedron Letters ,
1994
110.
Liu Z., Ruan X., Huang X.
Bioorganic and Medicinal Chemistry Letters ,
2003
111.
Romoff T.T., Ma L., Wang Y., Campbell D.A.
Synlett ,
1998
112.
Orsini P., Maccario A., Colombo N.
Synthesis ,
2007
113.
Knapp J.M., Fettinger J.C., Kurth M.J.
Organic Letters ,
2011
114.
Emtenäs H., Soto G., Hultgren S.J., Marshall G.R., Almqvist F.
Organic Letters ,
2000
115.
Pemberton N., Emtenäs H., Boström D., Domaille P.J., Greenberg W.A., Levin M.D., Zhu Z., Almqvist F.
Organic Letters ,
2005
116.
Emtenäs H., Carlsson M., Pinkner J.S., Hultgren S.J., Almqvist F.
Organic and Biomolecular Chemistry ,
2003
117.
Chorell E., Bengtsson C., Sainte-Luce Banchelin T., Das P., Uvell H., Sinha A.K., Pinkner J.S., Hultgren S.J., Almqvist F.
European Journal of Medicinal Chemistry ,
2011
118.
Pemberton N., Pinkner J.S., Edvinsson S., Hultgren S.J., Almqvist F.
Tetrahedron ,
2008
119.
Åberg V., Das P., Chorell E., Hedenström M., Pinkner J.S., Hultgren S.J., Almqvist F.
Bioorganic and Medicinal Chemistry Letters ,
2008
120.
Åberg V., Norman F., Chorell E., Westermark A., Olofsson A., Sauer-Eriksson A.E., Almqvist F.
Organic and Biomolecular Chemistry ,
2005
121.
Emtenäs H., Åhlin K., Pinkner J.S., Hultgren S.J., Almqvist F.
Journal of Combinatorial Chemistry ,
2002
122.
Emtenäs H., Taflin C., Almqvist F.
Molecular Diversity ,
2003
123.
SATO M., OGASAWARA H., YOSHIZUMI E., KATO T.
Chemical and Pharmaceutical Bulletin ,
2011
124.
Pemberton N., Jakobsson L., Almqvist F.
Organic Letters ,
2006
125.
Rubinov D.B., Rubinova I.L., Lakhvich F.A.
Russian Journal of Organic Chemistry ,
2011
126.
Grachev M.K., Edunov A.V., Kurochkina G.I., Popkov A.V., Levina I.I., Nifant’ev E.E.
Russian Journal of Organic Chemistry ,
2011
127.
Organic Syntheses ,
2000
128.
Sato M., Uehara F., Sato K., Yamaguchi M., Kabuto C.
Journal of the American Chemical Society ,
1999
129.
Habibi A., Eskandari K., Alizadeh A.
Phosphorus, Sulfur and Silicon and the Related Elements ,
2012
130.
SATO M., TAKAYAMA K., ABE Y., FURUYA T., INUKAI N., KANEKO C.
Chemical and Pharmaceutical Bulletin ,
2011
131.
Fillion E., Fishlock D., Wilsily A., Goll J.M.
Journal of Organic Chemistry ,
2005
132.
Fillion E., Wilsily A.
Journal of the American Chemical Society ,
2006
133.
Fillion E., Wilsily A., Liao E.
Tetrahedron Asymmetry ,
2006
134.
Dumas A.M., Fillion E.
Organic Letters ,
2009
135.
Wilsily A., Fillion E.
Journal of Organic Chemistry ,
2009