• Bulletin of the Korean Chemical Society
• /
• v.34 no.10
• /
• pp.2963-2967
• /
• 2013

This paper describes a simple and efficient method involving domino Knovenegal/$6{\pi}$ electrocyclization for the preparation of a variety of 2H-pyrans using microwave irradiation under solvent- and catalyst-free conditions. This method offers the advantages of a green approach, high yields, and short reaction times. Sixteen compounds (9a-p) were obtained in good to excellent yields using the procedure.

• Bulletin of the Korean Chemical Society
• /
• v.30 no.11
• /
• pp.2833-2836
• /
• 2009

• Bulletin of the Korean Chemical Society
• /
• v.7 no.5
• /
• pp.372-376
• /
• 1986

Substituted 3,4-dihydro-2H-pyrans ($1_{a-e}$) were prepared by (4 + 2) cycloaddition reaction of dimethyl dicyanofumarate with the corresponding electron-rich olefins. The compounds $1_{a-e}$ were ring-open polymerized by cationic initiators to obtain polymers of 1:1 alternating sequence. Polymerizations were carried out with boron trifluoride etherate in methylene chloride at $-78^{\circ}C$. All the polymers obtained were soluble in common solvents and were reprecipitated by pouring its chloroform solution into diethyl ether. All the compounds $1_{a-e}$ were not as reactive as the corresponding pyrans derived from ${\alpha}$ -cyanoacrylate.

• Bulletin of the Korean Chemical Society
• /
• v.23 no.7
• /
• pp.998-1002
• /
• 2002

An efficient synthesis of 2H-pyrans is achieved by indium (III) chloride-catalyzed reactions of 1,3-dicarbonyl compounds with a variety of $\alpha\beta-unsaturated$, aldehydes in moderate yields. This method has been applied to the synthesis of pyranocoumar ins, pyranophenalenones, and pyranoquinolinone alkaloids.

• Bulletin of the Korean Chemical Society
• /
• v.25 no.11
• /
• pp.1733-1736
• /
• 2004

• Bulletin of the Korean Chemical Society
• /
• v.22 no.8
• /
• pp.791-792
• /
• 2001

• Journal of the Korean Society of Industry Convergence
• /
• v.9 no.4
• /
• pp.331-336
• /
• 2006

An efficient synthesis of 3,4-dihydro-2H-pyrans is achieved by $Ag_2CO_3$/celite mediated reaction of 1,3-dicarbonyl compounds with vinyl ether in moderate yields. This method has been applied to the synthesis of 3,4-dihydro-2H-pyranochromens and 3,4-dihydro-2H-benzochromen. 3,4-Dihydro-2H-pyranochromens were easily converted to 4H-pyranochromens by elimination of ethoxy group. The structures of these compound were identified by IR and $^1H$ NMR-Spectra.

• Bulletin of the Korean Chemical Society
• /
• v.8 no.2
• /
• pp.102-105
• /
• 1987

2-Methoxy-6-methyl-3,4-dihydro-2H-pyran ($1_a$), 2-ethoxy-3,6-dimethyl-3,4-dihydro-2H-pyran ($1_b$), and 2-ethoxy-3-methyl-6-ethyl-3,4-dihydro-2H-pyran ($1_c$) were prepared by (4 + 2) cycloaddition reaction from the corresponding vinyl ketones and alkyl vinyl ethers. Compounds $1_{a-c}$ were ring-open polymerized by cationic catalyst to obtain alternating head-to-head (H-H) copolymers. For comparison, copolymer of head-to-tail (H-T) was also prepared by free radical copolymerization of the mixture of the corresponding monomers. The H-H copolymer exhibited some differences in its $^1H$ NMR and IR spectra. However, significant differences were showed between the H-H and H-T copolymers in the $^{13}C$ NMR spectra. Also noteworthy was that$T_g$ value of H-H copolymer was higher than that of the corresponding H-T structure. Decomposition temperature of the H-H copolymer was lower than that of the H-T copolymer. All the H-H and H-T copolymers were soluble in common solvents.

• Bulletin of the Korean Chemical Society
• /
• v.8 no.2
• /
• pp.96-101
• /
• 1987

2-Ethoxy-6-methoxy-5-cyano-3,4-dihydro-2H-pyran (1_a$), 2-n-butoxy-6-methoxy-5-cyano-3,4-dihydro-2H-pyr an (1b), 2-isobutoxy-6-methoxy-5-cyano-3,4-dihydro-2H-py ran ($1_c$), and 2-ethoxy-6-methoxy-3-methyl-5-cyano-3,4-dihydro -2H-pyran ($1_d$) were prepared by (4 + 2) cycloaddition reaction of methyl $\alpha$-cyanoacrylate with the corresponding alkyl vinyl ethers. Compounds $1_{a-d}$ were ring-open polymerized by cationic catalyst to obtain alternating head-to-head (H-H) copolymers. For comparison, head-to-tail (H-T) copolymer $3_a$ was also prepared by free radical copolymerization of the corresponding monomers. The H-H copolymer exhibited minor differences in its $1_H% NMR and IR spectra, but in the $^{13}C$ NMR spectra significant differences were observed between the H-H and H-T copolymers. Glass transition temperature ($T_g$) of H-H copolymer was higher than that of the H-T copolymer, but thermal decomposition temperature of the H-H copolymer was lower than that of the H-T copolymer. Compounds $1_a$, $a_b$, and $1_c$, copolymerized well with styrene by cationic catalyst, but compound 1d failed to copolymerize with styrene. All of the H-H and H-T copolymers were soluble in common solvents and the inherent viscosities were in the range 0.2-0.4 dl/g.

• Journal of the Korean Institute of Electrical and Electronic Material Engineers
• /
• v.17 no.1
• /
• pp.83-88
• /
• 2004

BAlq was fabricated as for hole blocking layer in the OLED devices to investigate its electrical and optical characteristics. Device structure was ITO/$\alpha$ -NPD/EML/BAlq/Alq3/Al:Li using TYG-201, DPVBi (4, 4 - Bis (2, 2 - diphenylethen-1 - yls) - Biphenyl), Alq and DCJTB (4-(dicyanomethylene)-2- (1-propyls)6-methy 4H-pyrans) as green emitting material, blue emitting material, host material for red emission and red emitting guest material respectively. The OLED device showed optimum working voltage and electron density at 600 cd/$m^2$ when thickness of BAlq is 25$\AA$ for RGB OLED devices while their efficiencies are better at 50$\AA$ of BAlq. Red and blue color OLEDs also fabricated using 30$\AA$ thickness of BAlq and compared with those without BAlq layer. BAlq was more effective in electrical properties such as working voltage, current density and efficiency of red OLED than blue and green ones. This study describes that 30$\AA$ is optimum thickness of BAlq for best performance of full color OLED devices when using BAlq as a hole blocking material.