Abstract
The nucleophile-induced rearrangement of cyclic N -alkoxy-N -(silyloxy)enamines was investigated.
As a result, a new strategy for the synthesis of β-pyranone
and β-furanone derivatives from nitro compounds is suggested.
Key words
nitroso acetals - rearrangement - nitrogen
heterocycles - 1,2-oxazines - aliphatic nitro compounds
References
1a Feger H.
Simchen G.
Liebigs
Ann. Chem.
1986,
1456
1b Dilman AD.
Tishkov AA.
Lyapkalo IM.
Ioffe SL.
Strelenko YuA.
Tartakovsky VA.
Synthesis
1998,
181
1c Dilman AD.
Tishkov AA.
Lyapkalo IM.
Ioffe SL.
Kachala VV.
Strelenko YuA.
Tartakovsky VA.
J.
Chem. Soc., Perkin Trans. 1
2000,
2926
2 Ioffe SL. In Nitrile Oxides, Nitrones and Nitronates in
Organic Synthesis
Feuer H.
John
Wiley & Sons;
Hoboken:
2008.
p.604
3 Tishkov AA.
Lesiv AV.
Khomutova YuA.
Strelenko YuA.
Nesterov ID.
Antipin MYu.
Ioffe SL.
Denmark SE.
J. Org. Chem.
2003,
68:
9477
4a Denmark SE.
Thorarensen A.
Chem.
Rev.
1996,
96:
137
4b Ioffe SL. In Nitrile Oxides,
Nitrones and Nitronates in Organic Synthesis
Feuer H.
John Wiley & Sons;
Hoboken:
2008.
444.
p.531
5a Kunetsky RA.
Dilman AD.
Struchkova MI.
Belyakov PA.
Tartakovsky VA.
Ioffe SL.
Synthesis
2006,
2265
5b For the synthesis of six-membered
cyclic nitronates from nitroethane, see ref.³
6a Elomri A.
Skaltsounis A.-E.
Michel S.
Tillequin F.
Koch M.
Rolland Y.
Pierre A.
Atassi G.
Chem. Pharm. Bull.
1996,
44:
2165
6b Wu ESC.
Griffith RC.
Loch JT.
Kover A.
Murray RJ.
Mullen GB.
Blosser JC.
Machulskis AC.
McCreedy SA.
J.
Med. Chem.
1995,
38:
1558
6c Tsukamoto S.
Fujii M.
Yasunaga T.
Matsuda K.
Wanibuchi F.
Hidaka K.
Furuya T.
Tamura T.
Chem. Pharm. Bull.
1995,
43:
842
6d Arora PK.
Kole PL.
Ray S.
Indian J. Chem., Sect. B: Org. Chem. Incl.
Med. Chem.
1985,
24:
845
7a Tsuda Y.
Okuno Y.
Iwaki M.
Kanemitsu K.
Chem. Pharm.
Bull.
1989,
37:
2673
7b Brehm M.
Goeckel VH.
Jarglis P.
Lichtenthaler FW.
Tetrahedron:
Asymmetry
2008,
19:
358
7c Jarglis P.
Goeckel VH.
Lichtenthaler FW.
Tetrahedron: Asymmetry
2009,
20:
952
8a Georgiadis MP.
Haroutounian SA.
Couladouros EA.
Apostolopoulos CD.
J. Heterocycl.
Chem.
1991,
28:
697
8b Georgiadis MP.
Haroutounian SA.
J.
Heterocycl. Chem.
1992,
29:
391
9 Tabolin AA.
Lesiv AV.
Khomutova YuA.
Nelyubina YuV.
Ioffe SL.
Tetrahedron
2009,
65:
4578
10 Cox DP.
Terpinski J.
Lawrynowicz W.
J.
Org. Chem.
1984,
49:
3216
11a Gerlach H.
Kuenzler P.
Helv.
Chim. Acta
1978,
61:
2503
11b Marti RE.
Heizner J.
Seebach D.
Liebigs Ann.
1995,
1193
12 Crystallographic data for the structure 4a have been deposited with the Cambridge
Crystallographic Data Centre as supplementary publication number
CCDC 805539. Copies of the data can be obtained, free of charge,
on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: +44(1223)336033;
E-mail: deposit@ccdc.cam.ac.uk.
13 Gottlieb HE.
Kotlyar V.
Nudelman A.
J.
Org. Chem.
1997,
62:
7512
14 Danilenko VM.
Tishkov AA.
Ioffe SL.
Lyapkalo IM.
Strelenko YA.
Tartakovsky VA.
Synthesis
2002,
635
15 Sukhorukov AYu.
Klenov MS.
Ivashkin PE.
Lesiv AV.
Khomutova YuA.
Ioffe SL.
Synthesis
2007,
97
16 Sukhorukov AY.
Lesiv AV.
Eliseev OL.
Khomutova YuA.
Ioffe SL.
Borissova AO.
Eur.
J. Org. Chem.
2008,
4025
17 Tabolin AA.
Lesiv AV.
Ioffe SL.
Synthesis
2009,
3099
18 Klenov MS.
Lesiv AV.
Khomutova YuA.
Nesterov ID.
Ioffe SL.
Synthesis
2004,
1159
19 Timms GH.
Wildsmith E.
Tetrahedron Lett.
1971,
195
