Covalent Analogues of DNA Base-Pairs and Triplets IV. Synthesis of Trisubstituted Benzenes Bearing Purine and/or Pyrimidine Rings by Cyclotrimerization of 6-Ethynylpurines and/or 5-Ethynyl-1,3-dimethyluracil

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Title:Covalent Analogues of DNA Base-Pairs and Triplets IV. Synthesis of Trisubstituted Benzenes Bearing Purine and/or Pyrimidine Rings by Cyclotrimerization of 6-Ethynylpurines and/or 5-Ethynyl-1,3-dimethyluracil
Creators:
Hocek, Michal
Stará, Irena G.
Starý, Ivo
Dvořáková, Hana
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 67, 8, pp. 1223-1235
Uncontrolled Keywords:Nickel, Hoogsteen triplets, Purines, [2+2+2] Cycloadditions, Nucleobases, Pyrimidines, Alkynes, Cyclotrimerizations

Abstract

Ni-Catalyzed cyclotrimerizations of 6-ethynylpurines <strong>3</strong> or 5-ethynyl-1,3-dimethyluracil (<strong>4</strong>) afforded the 1,2,4-tris(purin-6-yl)benzenes <strong>7</strong> or 1,2,4-tris(1,3-dimetyhyluracil-5-yl)benzene (<strong>9</strong>), respectively. The symmetrical 1,3,5-tris(purin-6-yl)benzenes <strong>8</strong> were also formed as minor products in very low yields. Co-cyclotrimerization of 9-benzyl-6-ethynylpurine (<strong>3a</strong>) with 4 afforded the tris(purinyl)benzene <strong>7a</strong> as a major product along with 1,2-bis(9-benzylpurin-6-yl)-4-(1,3-dimethyluracil-5-yl)benzene (<strong>10</strong>) and a complex mixture of other derivatives and isomers. Compounds <strong>7</strong>-<strong>10</strong> are analogues of Hoogsteen base-triplets. <p>

Title:Covalent Analogues of DNA Base-Pairs and Triplets IV. Synthesis of Trisubstituted Benzenes Bearing Purine and/or Pyrimidine Rings by Cyclotrimerization of 6-Ethynylpurines and/or 5-Ethynyl-1,3-dimethyluracil
Creators:
Hocek, Michal
Stará, Irena G.
Starý, Ivo
Dvořáková, Hana
Uncontrolled Keywords:Nickel, Hoogsteen triplets, Purines, [2+2+2] Cycloadditions, Nucleobases, Pyrimidines, Alkynes, Cyclotrimerizations
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:67
Number:8
Page Range:pp. 1223-1235
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20021223UNSPECIFIED
ID Code:1986
Item Type:Article
Deposited On:06 Feb 2009 17:14
Last Modified:06 Feb 2009 16:14

Citation

Hocek, Michal; Stará, Irena G.; Starý, Ivo; Dvořáková, Hana (2002) Covalent Analogues of DNA Base-Pairs and Triplets IV. Synthesis of Trisubstituted Benzenes Bearing Purine and/or Pyrimidine Rings by Cyclotrimerization of 6-Ethynylpurines and/or 5-Ethynyl-1,3-dimethyluracil. Collection of Czechoslovak Chemical Communications, 67 (8). pp. 1223-1235. ISSN 0010-0765

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