A new synthetic route to 2-hydroxynaphthalene-1-carboxylic acid derivatives. An efficient access to the naphthalene moiety of neocarzinostatin chromophore

We report the synthesis of pyrene-conjugated azanucleoside-incorporated oligodeoxynucleotides (aza-ODNs). Combination of liquid-phase synthesis by alkyl-chain-soluble-support (ACSS) and electrochemical C–H activation realized efficient access to aza-ODNs without requiring an excess amount of reagent or solvent. The fluorescent properties of pyrene-conjugated aza-ODNs were also investigated. The resulting fluorescence spectrum indicated that the modification of the position of the nitrogen atom was suitable for the preparation of artificial functionalized oligonucleotides. A synthetic route to azaribose, as a precursor of aza-ODNs, was also reinvestigated to realize more efficient production. Electrochemical N-α-acetoxylation in 0.1 M lithium perchlorate/nitromethane/50 mM AcOH medium was found to be a suitable medium for this route. These results represent a new efficient synthetic route to aza-ODNs.

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A new synthetic route to 7-halo-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, an intermediate for the synthesis of quinolone antibacterial agents

Journal of Heterocyclic Chemistry ◽

10.1002/jhet.5570240134 ◽

1987 ◽

Vol 24 (1) ◽

pp. 181-185 ◽

Cited By ~ 16

Author(s):

Hiroshi Egawa ◽

Masahiro Kataoka ◽

Koh-Ichiro Shibamori ◽

Teruyuki Miyamoto ◽

Junji Nakano ◽

...

Keyword(s):

Carboxylic Acid ◽

Antibacterial Agents ◽

Synthetic Route

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Energy efficient Pfitzinger reaction: a novel strategy using a surfactant catalyst

New Journal of Chemistry ◽

10.1039/c7nj01937h ◽

2017 ◽

Vol 41 (21) ◽

pp. 12380-12383 ◽

Cited By ~ 4

Author(s):

Priyanka A. More ◽

Ganapati S. Shankarling

Keyword(s):

Carboxylic Acid ◽

Energy Efficient ◽

Synthetic Route ◽

Pfitzinger Reaction ◽

Ultrasound Assisted ◽

Novel Strategy

A novel ultrasound assisted synthetic route catalysed by a surfactant for the synthesis of quinolone-4-carboxylic acid.

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On the synthesis of cryptosporiopsin: stereochemistry of early intermediates

Canadian Journal of Chemistry ◽

10.1139/v82-292 ◽

1982 ◽

Vol 60 (16) ◽

pp. 2062-2064

Author(s):

George M. Strunz ◽

Peter S. White

Keyword(s):

Carboxylic Acid ◽

Methyl Ester ◽

Single Crystal ◽

Acid Methyl Ester ◽

Direct Methods ◽

Monoclinic Space Group ◽

Synthetic Route ◽

Space Group ◽

X Ray ◽

Acid Methyl

The relative configurations of two intermediates in the synthetic route to cryptosporiopsin are clarified through the structure of 3,5-dichloro-1,4-dihydroxy-2-methylcyclopent-2-ene-1-carboxylic acid methyl ester, which was determined by single crystal X-ray techniques. The crystal was monoclinic, space group P21/c, a = 7.352(1), b = 8.868 (3), c = 16.300(7) Å; β = 96.49(2)°. The structure was solved by direct methods and refined to a final R of 0.057.

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