Synthesis method of 6-substituted phenanthridine compound

Abstract

The invention discloses a synthesis method of a 6-substituted phenanthridine compound represented by a formula (I), wherein a N-[1-phenyl-1'-biphenyl]benzenesulfonamide compound represented by a formula (II) is used as a raw materials and is subjected to a reaction in an organic solvent under the action of a [Fe] / Selectfluor catalyst to prepare a corresponding target product represented by the formula (I). According to the present invention, the synthesis method has advantages of environmental friendliness, mild reaction conditions, good functional group popularity, easy operation and the like, and uses the catalyst with advantages of low cost, easy availability and low toxicity. The formulas (I) and (II) are defined in the specification.

Description

(1) Technical field [0001] The invention relates to a method for synthesizing organic compounds, in particular to a method for synthesizing 6-substituted phenanthridine compounds. (2) Background technology [0002] Phenanthridine widely exists in a series of diverse compound structures, including a wide range of important natural products, compounds with antiviral, antiprotozoal and antitumor biological and drug therapeutic activities and functional material compounds. The molecule contains this Fragments have received considerable attention in medicine and materials, so that chemists have focused most of their efforts on the synthesis of phenanthridine derivatives. Therefore, research and development of related synthesis technologies of phenanthridine derivatives 6-substituted phenanthridines have broad application prospects. [0003] At present, the synthetic method of relevant 6-substituted phenanthridines reported at home and abroad mainly contains the following several...

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Problems solved by technology

[0003] At present, the synthetic method of relevant 6-substituted phenanthridines reported at home and abroad mainly contains the following several methods: (1) adopt Bischler-Napieralski cyclization method (referring to J.Chem.Soc.1950,703-711 and J.Chem. Soc.1957,505-509), this method needs to add P 4 o 10 , POCl 3 or PCl 5 , Harsh conditions limit the synthesis of a variety of resistant functional groups, so that the synthesis of some compounds is limited; (2) Synthesis by cyclization of o-aryl benzohydroxime under microwave conditions (see J.Org.Chem.2008,73, 5558), the mechanism of this method is a free radical reaction, and its reaction temperature requirement is relatively high (above 100 degrees); (3) use fluorinated aromatic hydrocarbons and nitriles as raw materials, synthesized through 1,2-aryne intermediates (see Org.Lett .2002,4,2687.), this method has many reaction steps and high requirements on the control of reaction temperature; (4) using o-aryl oxime carbonate as raw material, promoting cyclization by photocatalysis and taking off a part of alcohol and carbon dioxide to synthesize (See Chem.Commun.2011,47,7974–7976), the photochemical reaction of this method requires the high dilution of the reaction solution and the use of a stoichiometric sensitizer; (5) using benzylamine and aryl iodide as raw materials, through Palladium catalyst catalytic activation synthesis (see Org.Lett.2010,12,5692), this method is a transition metal catalysis method, the reaction temperature requirements are high, the reaction time is long, the use of expensive noble metal catalysts and the need to add toxic organic phosphorus compounds As a ligand, the conditions are more stringent

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