3-quinolinecarboxylicacid,1,4-dihydro-1- CIPROBAY 85721-33 ...
Supplementary Information Synthesis of 2,3-Dihydro-4 ... · Supplementary Information Synthesis of...
Transcript of Supplementary Information Synthesis of 2,3-Dihydro-4 ... · Supplementary Information Synthesis of...
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Supplementary Information
Synthesis of 2,3-Dihydro-4-pyranones from Epoxides via Intermolecular [4+2] Cycloaddition Reaction
Kiran Indukuri, Somasekhar Bondalapati, Sabera Sultana and Anil K. Saikia*
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Experimental Section
General
All the reagents are commercially obtained. BF3·Et2O was distilled over CaH2 prior to use.1H NMR spectra were recorded in CDCl3 on Varian AS 400 (400 MHz) spectrometer using TMS as internal standard. The 13C spectra were obtained on Varian AS 400 operating at 100 MHz. IR spectra were recorded on Nicolet Impact 410 FT-IR spectrometer. HRMS spectra were recorded using ESI mode. Melting points were measured in open capillary tubes and are uncorrected. All 3-ethoxy cyclobutanones are prepared by the following literature methods. Ref: 1) J.-i. Matsuo, R. Okuno, K. Takeuchi, M. Kawano and H. Ishibashi, Tetrahedron Lett. 2010, 51, 3736. 2) J.-i. Matsuo, S. Sasaki, H. Tanaka and H. Ishibashi, J. Am. Chem. Soc. 2008, 130, 11600.
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1H NMR spectrum of 1
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OO
OO
cis:trans=1:8
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13C NMR spectrum of 1
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OO
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1H NMR spectrum of 2
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OO
OO
cis:trans=1:8
Br
Br
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13C NMR spectrum of 2
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OO
Br
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1H NMR spectrum of 3
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OO
OO
cis:trans=1:9
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13C NMR spectrum of 3
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OO
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1H NMR spectrum of 4
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OO
OO
cis:trans=1:8
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13C NMR spectrum of 4
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OO
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1H NMR spectrum of 5
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OO
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13C NMR spectrum of 5
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OO
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1H NMR spectrum of 6
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OO
Cl
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13C NMR spectrum of 6
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OO
Cl
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1H NMR spectrum of 7
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OO
PhPh
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13C NMR spectrum of 7
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OO
PhPh
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1H NMR spectrum of 8
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OO
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13C NMR spectrum of 8
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OO
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1H NMR spectrum of 9
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OO
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13C NMR spectrum of 9
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OO
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1H NMR spectrum of 10
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OO
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13C NMR spectrum of 10
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OO
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1H NMR spectrum of 13
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OO
OO
cis:trans=1:17
Ph
Ph
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13C NMR spectrum of 13
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OO
Ph
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1H NMR spectrum of 14
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OO
OO
cis:trans=1:12
Ph
PhMe
Me
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13C NMR spectrum of 14
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OO
PhMe
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1H NMR spectrum of 15
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OO
OO
cis:trans=1:8
Ph
Ph
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13C NMR spectrum of 15
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OO
Ph
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1H NMR spectrum of 16
S29
OO
Br
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13C NMR spectrum of 16
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OO
Br
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1H NMR spectrum of 17
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OO
OO
cis:trans=1:5
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13C NMR spectrum of 17
S32
OO
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1H NMR spectrum of 18
S33
cis:trans=1 :7
OO
OO
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13C NMR spectrum of 18
S34
OO
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