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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/01/11 11:56:15」(JST)

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Phenanthridine is a nitrogen heterocyclic compound that is the basis of DNA-binding fluorescent dyes through intercalation. Examples of such dyes are ethidium bromide and propidium iodide. Acridine is an isomer of phenanthridine.

Phenanthridine was discovered by Amé Pictet and H. J. Ankersmit in 1891 by pyrolysis of the condensation product of benzaldehyde and aniline.^[2] In the Pictet–Hubert reaction (1899) the compound is formed in a reaction of the 2-aminobiphenyl – formaldehyde adduct (an N-acyl-o-xenylamine) with zinc chloride at elevated temperatures.^[3]

The reaction conditions for the Pictet–Hubert reaction were improved by Morgan and Walls in 1931, replacing the metal by phosphorus oxychloride and using nitrobenzene as a reaction solvent.^[4] For this reason, the reaction is also called the Morgan–Walls reaction.^[5]

The reaction is similar to the Bischler–Napieralski reaction and the Pictet–Spengler reaction.

References

^ Lide, David R. (1998), Handbook of Chemistry and Physics (87 ed.), Boca Raton, FL: CRC Press, pp. 3–460, ISBN 0-8493-0594-2
^ Mittheilung Ueber das Phenanthridin Amé Pictet, H. J. Ankersmit Chemisches Laboratorium der Universität Genf Justus Liebigs Annalen der Chemie Volume 266 Issue 1-2, pp. 138–153 doi:10.1002/jlac.18912660107
^ Mittheilungen Ueber eine neue Synthese der Phenanthridinbasen Amé Pictet, A. Hubert Berichte der deutschen chemischen Gesellschaft Volume 29 Issue 2, pp. 1182–1189, 1896 doi:10.1002/cber.18960290206
^ CCCXXXV.—Researches in the phenanthridine series. Part I. A new synthesis of phenanthridine homologues and derivatives Gilbert T. Morgan, Leslie Percy Walls, J. Chem. Soc., 1931, 2447–2456 doi:10.1039/JR9310002447
^ Jie Jack Li (ed.), 2004, Name Reactions in Heterocyclic Chemistry, Wiley.

English Journal

Synthesis of pyrazolo[4,3-a]phenanthridines, a new scaffold for Pim kinase inhibition.

Suchaud V1, Gavara L1, Giraud F1, Nauton L1, Théry V1, Anizon F2, Moreau P3.
Bioorganic & medicinal chemistry.Bioorg Med Chem.2014 Sep 1;22(17):4704-10. doi: 10.1016/j.bmc.2014.07.011. Epub 2014 Jul 16.
A new series of nitro or amino substituted pyrazolo[4,3-a]phenanthridines was synthesized in 6 steps from 5-bromo-6-nitroindazole. The evaluation of their inhibitory potency toward Pim kinases demonstrated that the nitro series could be considered as an interesting starting point for the development
PMID 25087047

New methods for the synthesis of naphthyl amines; application to the synthesis of dihydrosanguinarine, sanguinarine, oxysanguinarine and (±)-maclekarpines B and C.

Tatton MR1, Simpson I, Donohoe TJ.
Chemical communications (Cambridge, England).Chem Commun (Camb).2014 Aug 28;50(77):11314-6. doi: 10.1039/c4cc05209a.
A new method for preparing naphthyl amines from 1,5 unsaturated dicarbonyl precursors is described; the utility of this new method was proven in the syntheses of several natural products, all containing the benzo[c]phenanthridine core and enabled by a radical promoted cyclisation of the naphthyl ami
PMID 25116797

A cascade alkylarylation reaction of 2-isocyanobiphenyls with simple alkanes for 6-alkyl phenanthridines via dual C(sp3)-H/C(sp2)-H functionalizations.

Zhu ZQ1, Wang TT, Bai P, Huang ZZ.
Organic & biomolecular chemistry.Org Biomol Chem.2014 Aug 21;12(31):5839-42. doi: 10.1039/c4ob01256a.
A cascade alkylarylation reaction of 2-isocyanobiphenyls with simple alkanes for 6-alkyl phenanthridines has been developed through dual C(sp(3))-H/C(sp(2))-H functionalizations. The synthetic method has the advantages of high yields, good compatibility of functional groups and mild reaction conditi
PMID 24995431

Japanese Journal

TOTAL SYNTHESIS OF THE BENZO[c]PHENANTHRIDINE ALKALOIDS, TERIHANINE AND ISOTERIHANINE, AND THEIR ANTITUMOR ACTIVITY (Dedicated to Professor Victor Snieckus on the occasion of his 77th birthday)

Kurata Yuhki,Choshi Tominari,Ishihara Yuhsuke [他]
Heterocycles : an international journal for reviews and communications in heterocyclic chemistry 88(1), 297-308, 2014-01-01
NAID 40019928292

Synthesis and in Vitro Antifungal Activities of New 2-Aryl-6,7-methylenedioxy-3,4-dihydroisoquinolin-2-ium Bromides

, , [他], , , ,
Chemical and Pharmaceutical Bulletin 61(7), 731-739, 2013
… 2-Aryl-3,4-dihydroisoquinolin-2-iums might be considered as a class of simple analogues of natural quaternary benzo[c]phenanthridine alkaloids. …
NAID 130003360807

ベンゾ[C]フェナンスリジン・アルカロイドおよび関連化合物の合成研究

石川勉
有機合成化学協会誌 70(1), 17-29, 2012-01-01
… Benzo[c]phenanthridine alkaloids are distributed in Papaveraceous and Rutaceous plants and classified into two categories of fully aromatized bases and partially hydrogenated bases(B/C-cis-11-hydroxyhexahydrobenzo[c]phenanthridine skeleton). … Thus, in this review, we present our chemical history for the synthesis of benzo[c]phenanthridine bases. …
NAID 10030480737

Related Pictures

-16-9,Pyrido(2,3,4,5-lmn)phenanthridine Narcissidine is a phenanthridine alkaloid for [1,2,3]triazolo[1,5-f]phenanthridine Ähnlich verlaufen Cyclisierungsreaktionen PHENANTHRIDINE ALKALOIDS millimetre wave spectrum of phenanthridine Phenanthridin - Phenanthridine.svg

★リンクテーブル★

リンク元	「フェナンスリジン」「フェナントリジン」
拡張検索	「benzophenanthridine」

「フェナンスリジン」

Phenanthridine
Names
	IUPAC name phenanthridine
Identifiers
CAS Number	229-87-8
3D model (Jmol)	Interactive image
ChEBI	CHEBI:36421
ChemSpider	8834
ECHA InfoCard	100.005.396
EC Number	205-934-4
PubChem	9189
	InChI InChI=1S/C13H9N/c1-2-6-11-10(5-1)9-14-13-8-4-3-7-12(11)13/h1-9H Key: RDOWQLZANAYVLL-UHFFFAOYSA-N ; InChI=1/C13H9N/c1-2-6-11-10(5-1)9-14-13-8-4-3-7-12(11)13/h1-9H Key: RDOWQLZANAYVLL-UHFFFAOYAL ;
	SMILES C1=CC=C2C(=C1)C=NC3=CC=CC=C23 ;
Properties
Chemical formula	C13H9N
Molar mass	179.217 g/mol
Melting point	107.4 °C (225.3 °F; 380.5 K)
Boiling point	348.9 °C (660.0 °F; 622.0 K)
Solubility in water	slightly soluble
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references