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On the Synthesis of Isomeric Dithiophene Analogues of Phenathridine- N-oxides

Salo Gronowitz ; Division of Organic Chemistry 1, Chemical Center, University of Lund, P.O. Box 124, S-221 00 Lund, Sweden
Anna-Britta Hornfeldt ; Division of Organic Chemistry 1, Chemical Center, University of Lund, P.O. Box 124, S-221 00 Lund, Sweden
Youhua Yang ; Division of Organic Chemistry 1, Chemical Center, University of Lund, P.O. Box 124, S-221 00 Lund, Sweden

Puni tekst: engleski, pdf (6 MB) str. 313-326 preuzimanja: 148* citiraj
APA 6th Edition
Gronowitz, S., Hornfeldt, A. i Yang, Y. (1986). On the Synthesis of Isomeric Dithiophene Analogues of Phenathridine- N-oxides. Croatica Chemica Acta, 59 (1), 313-326. Preuzeto s https://hrcak.srce.hr/177596
MLA 8th Edition
Gronowitz, Salo, et al. "On the Synthesis of Isomeric Dithiophene Analogues of Phenathridine- N-oxides." Croatica Chemica Acta, vol. 59, br. 1, 1986, str. 313-326. https://hrcak.srce.hr/177596. Citirano 21.06.2021.
Chicago 17th Edition
Gronowitz, Salo, Anna-Britta Hornfeldt i Youhua Yang. "On the Synthesis of Isomeric Dithiophene Analogues of Phenathridine- N-oxides." Croatica Chemica Acta 59, br. 1 (1986): 313-326. https://hrcak.srce.hr/177596
Harvard
Gronowitz, S., Hornfeldt, A., i Yang, Y. (1986). 'On the Synthesis of Isomeric Dithiophene Analogues of Phenathridine- N-oxides', Croatica Chemica Acta, 59(1), str. 313-326. Preuzeto s: https://hrcak.srce.hr/177596 (Datum pristupa: 21.06.2021.)
Vancouver
Gronowitz S, Hornfeldt A, Yang Y. On the Synthesis of Isomeric Dithiophene Analogues of Phenathridine- N-oxides. Croatica Chemica Acta [Internet]. 1986 [pristupljeno 21.06.2021.];59(1):313-326. Dostupno na: https://hrcak.srce.hr/177596
IEEE
S. Gronowitz, A. Hornfeldt i Y. Yang, "On the Synthesis of Isomeric Dithiophene Analogues of Phenathridine- N-oxides", Croatica Chemica Acta, vol.59, br. 1, str. 313-326, 1986. [Online]. Dostupno na: https://hrcak.srce.hr/177596. [Citirano: 21.06.2021.]

Sažetak
Six of nine o,o'-formylnitrobithienyls have been synthesized
by the tetrakis(triphenylphosphine)palladium(O)-catalyzed coupling
of the three o-bromonitrothiophenes with two of the three o-formylthiopheneboronic acids with sodium carbonate or sodium bicarbonate as base and an ethylene glycol dimethyl ether-water
mixture as solvent. In the reaction with 3-formyl-2-thiopheneboronic
acid, the coupling was carried out by using triethylamine
as base and N,N-dimethylformamide as solvent in an attempt to
avoid the facile deboronation of 3-formyl-2-thiopheneboronic acid,
but without success. Reduction of the o,o'-formylnitrobithienyls gave high yields of the N-oxides of the six isomeric dithienopyridines, which are analogues of phenanthridine-N-oxide. A direct synthesis of one of
the dithienopyridines, dithieno[2,3-c:2',3'-c]-pyridine, was achieved
by the palladium(O)-catalyzed coupling of 2,3-dibromothiophene
with 2-formyl-3-thiopheneboranic acid to 3-bromo-2'-formyl-2,3'-
-bithienyl, which was transformed to the 3-azido-2'-formyl-2,3'-
-bithienyl, which upon reduction with hydrogen sulfide underwent
ring closure to the phenanthridine analogue.

Hrčak ID: 177596

URI
https://hrcak.srce.hr/177596

Posjeta: 232 *