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Molecules 2012, 17(6), 6519-6546; doi:10.3390/molecules17066519
Article

Development of Diversified Methods for Chemical Modification of the 5,6-Double Bond of Uracil Derivatives Depending on Active Methylene Compounds

1,* , 1, 1, 1, 1, 1,†, 1,‡, 2,# and 1,§,*
Received: 28 April 2012; in revised form: 21 May 2012 / Accepted: 21 May 2012 / Published: 30 May 2012
(This article belongs to the Special Issue Nucleic Acid Analogs)
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Abstract: The reaction of 5-halogenouracil and uridine derivatives 1 and 7 with active methylene compounds under basic conditions produced diverse and selective C-C bond formation products by virtue of the nature of the carbanions. Three different types of reactions such as the regioselective C-C bond formation at the 5- and 6-positions of uracil and uridine derivatives (products 2, 5, 8, 17, 20 and 21), and the formation of fused heterocycle derivatives 2,4-diazabicyclo[4.1.0]heptane (15) and 2,4-diazabicyclo-[4.1.0]nonane (16) via dual C-C bond formations at both the 5- and 6-positions were due to the different active methylene compounds used as reagents.
Keywords: C-C bond formation; active methylene; carbanion; uracil; uridine C-C bond formation; active methylene; carbanion; uracil; uridine
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Sajiki, H.; Iida, Y.; Ikawa, K.; Sawama, Y.; Monguchi, Y.; Kitade, Y.; Maki, Y.; Inoue, H.; Hirota, K. Development of Diversified Methods for Chemical Modification of the 5,6-Double Bond of Uracil Derivatives Depending on Active Methylene Compounds. Molecules 2012, 17, 6519-6546.

AMA Style

Sajiki H, Iida Y, Ikawa K, Sawama Y, Monguchi Y, Kitade Y, Maki Y, Inoue H, Hirota K. Development of Diversified Methods for Chemical Modification of the 5,6-Double Bond of Uracil Derivatives Depending on Active Methylene Compounds. Molecules. 2012; 17(6):6519-6546.

Chicago/Turabian Style

Sajiki, Hironao; Iida, Yusuke; Ikawa, Kanoko; Sawama, Yoshinari; Monguchi, Yasunari; Kitade, Yukio; Maki, Yoshifumi; Inoue, Hideo; Hirota, Kosaku. 2012. "Development of Diversified Methods for Chemical Modification of the 5,6-Double Bond of Uracil Derivatives Depending on Active Methylene Compounds." Molecules 17, no. 6: 6519-6546.


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