Expeditious Entry to Novel 2-Methylene-2,3-dihydrofuro[3,2-c] chromen-2-ones from 6-Chloro-4-hydroxychromen-2-one and Propargylic Alcohols
Abstract
:1. Introduction
2. Results and Discussion
Distances | |
C8-C9 | 1.338(3) |
C9-O3 | 1.360(2) |
O3-C10 | 1.417(2) |
C10-C11 | 1.321(3) |
C10-C12 | 1.523(3) |
C12-C8 | 1.507(3) |
C7-O1 | 1.393(3) |
C7-O2 | 1.211(3) |
C1-Cl1 | 1.738(2) |
Angles | |
C8-C9-O3 | 114.13(18) |
C9-O3-C10 | 106.39(16) |
O3-C10-C11 | 118.8(2) |
C11-C10-C12 | 131.1(2) |
O3-C10-C12 | 110.07(16) |
C10-C12-C8 | 99.46(17) |
C12-C8-C9 | 109.77(18) |
3. Experimental
3.1. General
3.2. Synthesis of the 8-chloro-2-methylene-2,3-dihydrofuro[3,2-c]chromen-2-ones 4a–d
3.3. Synthesis of 8-chloro-3-(2-methoxyphenyl)-2-methyl-furo[3,2-c]chromen-2-one (5b)
3.4. X-ray Crystal Structure Determination of Compound 4a
Empirical formula | C19H13O4Cl |
Formula weight | 340.74 |
Temperature | 150(2) K |
Wavelength | 1.5418 Å |
Crystal system, space group | triclinic, P-1 |
Unit cell dimensions | a = 4.8366(2) Å α = 94.822(4)° |
b = 11.0016(5) Å β = 90.363(4)° | |
c = 14.6466(7) Å γ = 94.200(4)° | |
Volume | 774.45(6) Å3 |
Z, calculated density | 2, 1.461 mg/m3 |
Absorption coefficient | 2.369 mm−1 |
F(000) | 352 |
Crystal size | 0.37 × 0.03 × 0.02 mm |
Theta range for data collection | 3.03 to 73.76° |
Limiting indices | −4 ≤ h ≤ 6, −13 ≤ k ≤ 12, −17 ≤ l ≤ 17 |
Reflections collected / unique | 7403/2919 (Rint = 0.0214) |
Completeness to theta = 73.76º | 93.4% |
Refinement method | Full-matrix least-squares on F2 |
Data / restrains / parameters | 2919/0/269 |
Goodness-of-fit on F2 | 1.166 |
Final R indices [I > 2sigma(I)] | R1 = 0.0411, wR2 = 0.1177 |
R indices (all data) | R1 = 0.0517, wR2 = 0.1354 |
Largest diff. peak and hole | 0.334 and −0.267 e∙Å3 |
4. Conclusions
Acknowledgments
Conflict of Interest
References and Notes
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Nebra, N.; Díaz-Álvarez, A.E.; Díez, J.; Cadierno, V. Expeditious Entry to Novel 2-Methylene-2,3-dihydrofuro[3,2-c] chromen-2-ones from 6-Chloro-4-hydroxychromen-2-one and Propargylic Alcohols. Molecules 2011, 16, 6470-6480. https://doi.org/10.3390/molecules16086470
Nebra N, Díaz-Álvarez AE, Díez J, Cadierno V. Expeditious Entry to Novel 2-Methylene-2,3-dihydrofuro[3,2-c] chromen-2-ones from 6-Chloro-4-hydroxychromen-2-one and Propargylic Alcohols. Molecules. 2011; 16(8):6470-6480. https://doi.org/10.3390/molecules16086470
Chicago/Turabian StyleNebra, Noel, Alba E. Díaz-Álvarez, Josefina Díez, and Victorio Cadierno. 2011. "Expeditious Entry to Novel 2-Methylene-2,3-dihydrofuro[3,2-c] chromen-2-ones from 6-Chloro-4-hydroxychromen-2-one and Propargylic Alcohols" Molecules 16, no. 8: 6470-6480. https://doi.org/10.3390/molecules16086470