Naphtho quinoline

H-Cyclopenta[7,8]naphtho[2,3-6]furan-7-yl glyoxylate, 2,3,6,10-tetrahydro-6-hydroxy-6-methyl-3,10-dioxo-, methyl ester H NMR. 4, 560 (66JCS(C)743) Cyclopenta[6]quinoline, 6,7,8,9-tetrahydro- C NMR, 2, 122 (77JOC300, 77JOC2742)... 

Naphtho[l,2-h]pyrylium salts, 5,6-dihydro-2,4-diphenyl-synthesis, 3, 869 Naphtho[2,l-h]pyrylium salts synthesis, 3, 866 Naphthoquinolines, tetrahydro-synthesis, 2, 469 N aphtho[ 1,2-7]quinolines Skraup synthesis, 2, 467... 

The ring closure of diethyl (benzo[/]quinolin-l-yl)methylenemalonate (148) was carried out by heating in polyphosphoric acid at 90-110°C to give ethyl naphtho[ 1,2,3-//]quinolizine-6-carboxylate (723) (84USP4456606). 

Castle and co-workers <1996JHC119, 1996JHC185, 1997JHC1597, 1998JHC1441> used 3-chlorothieno [2,3-3]thiophene-2-carbonyl chloride 280 in the synthesis of the appropriate amides, which by oxidative photo-cyclization gave novel polycyclic heterocyclic ring systems thieno[3, 2 4,5]thieno[2,3-f][l,10]phenanthroline 281, thieno[3, 2 4,5]thieno[2,3-f]naphtho[2,iy ]quinoline 282 and thieno[3, 2 4,5]thieno[2,3-f]naphtho[l,2-g]qui-noline 283, thieno[3, 2 4,5]thieno[2,3-f]naphtho[l,2y ]quinoline 284, thieno[3, 2 4,5]thieno[2,3-f]naphtho[l,2 7]-[l,2,4]triazolo[3,4- ]quinoline 286, thieno[3, 2 4,5]thieno[2,3-f]naphtho[l,2-/]tetrazolo[l,5- ]quinoline 288, benzo[ ]thieno[3, 2 4,5]thieno[2,3-f]quinoline 285, benzo /]thieno[3, 2 4,5]thieno[2,3-f]quinoline 287, benzol/] thieno[3, 2 4,5]thieno[2,3-f]tetrazolo[l,5- ]quinoline 289, and benzo[/jthieno[3, 2 4,5]thieno[2.3-f][l,2,4]triazolo[4,3- ]-quinoline 290. 

Naphthof 1,2 -/] quinoline Naphtho[2,1 -/]quinoline Benzo[c]phenanthridine Benzo[i]phenanthridine Benz[o]acridine... 

See Fig. 9 for data on benz[a]acridine, benz[c]acridine, naphtho[2,3- ]quinoline, naphth[2,3- ]iaoquinoline, benz[6]acridine, dibenz[6,fe]acridine, see ref. 7. 

Naphtho[ 1,2-/] quinoline Lowest means a before b before c, etc. 

The nomenclature of peri-naphthalene heterocycles does not follow a common principle. In many original papers, the names of heterocyclic systems are derived from the corresponding peri-annelated hydrocarbon derivatives (1,2-diazaacenaphthylene, 1-oxaphenalene, etc.), from monoheterocycles with an indication of linked positions (naphtho[l,8-6c]furan, naphtho[l,8-de]azepine, etc.), and from benzoannelated heterocycles (benzo[o/]indole, benzo[heterocyclic systems and some compounds have trivial names, for instance, perimidine, naph-thostyryl, and naphtholactone. Moreover, it is necessary to remember some peculiarities in the electronic structure of peri-annelated heterocycles, namely the absence of independent existance of the 7r-closed-loop monoheterocycles which could be a fragment of peri-annelated heterocyclic systems. Therefore, the separation of a heterocycle from the united 7r-system is impossible. In this case, the simplest structure and the tt-electron unit is the whole peri-heterocyclic nucleus. 

Cyclization of 6-(arylcarbonyl)methyl-2-aryl-77/-naphtho[l,2,3-with hydrazine hydrate gave 1,2-diazepine derivatives 61 <2003AJC1219> (Equation 6). 

Intramolecular carbenoid and nitrenoid insertions are also quite effective for the preparation of peri-condensed heterocycles. Thus, photolysis of 1-naphthyl-1,2,3-triazoles 113 leads to bcnzo[d,e quinolines 115, possibly via carbene intermediate 114 (Scheme 55) <1987J(P1)413>. Similarly, on photolysis or thermolysis of 8-azido-l-arylazonaphtha-lenes 116 naphtho[l,8-<7, ]triazine derivatives 117 are formed along with A-aryhminobenzo[/y/]indazoles 118 (Scheme 56) <1978JOC2508, 1982JOC1996>. 

Substituted benzo[c]furans played a very important role in the quest for natural as well as non-natural molecules. The schemes depicted here are examples showing the use of substituted benzo[f]furans in the synthesis of complex molecules. A short synthesis of ( )-halenaquinone 173 was reported <2001JOC3639>, in which the pivotal step was the Diels-Alder cycloaddition of 4,7-dimethoxybenzo[f]furan 171 to 172, as illustrated in Scheme 62. In a similar manner, the total synthesis of ( )-xestoquinone, ( )-9-methoxyxestoquinone, ( )-10-methoxyxestoquinone <2001T309>, and the naphtho[2,3- ]quinoline portion of dynemicin A <1997JA5591> was also achieved. 

Isocyanat 2-Cyan-2-methyl-l-phenyl-ethenyl- E4, 798 (2-NH2-en-CN + COCl2) Isoquinolo 4,3-d -l,3-oxazol 2-Methyl- E8a, 1088 (4-N3-iso-quinolin + H3C —COOH) Malonaldehydsiinre (4-Cyanmethyi-phenyl)- -nitril E3, 15 Naphtho(2,3-d -l,2-oxazol 3-Amino-E8a, 242 [2-OH — naphth. — 3-C(NH2)=N — O — COOR/A] lH-< Naphtho 1,8a,8-d,e]pyrimidin) ... 

Further details have appeared of the one jx)t synthesis of naphtho[2,l-g]quinoline-7,12-dione derivatives (250) from irradiation of the quinolinedione (251a) in the presence of l,l-diarylethylenes. The same workers have more fully described their earlier findings on the formation of (252) and thence (253) from the photoinduced reaction of dichloronaphtho-1,4-quinone (251b) and the ethylenes. In this latter system, CIDNP studies have... 

Intermolecular photoelimination of HX has been employed in the syntheses of naphtho[2,l-g]quinoline-7,12-diones, of polycyclic quinones/ and of S-phenylpyridines the reaction has also found use in the trifluoromethyla-tion of imidazoles. ... 

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