Photolysis of 2-amino- and 2-methylamino-1,4-naphthoquinone

Martins, Charles Ferreira; Viljoen, A. M.; Strydom, S. J.; Fourie, L.; Wessels, Philippus L.

doi:10.1016/s0040-4020(01)85846-4

Cited by 11 publications

(3 citation statements)

References 5 publications

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“…Upon thermal cyclization of 55 with ethyl 2,2‐diethoxyacetate ( 95 ), 6 H ‐dibenzo[ b , i ]carbazole‐5,13:7,12‐diquinone ( 96 ) was obtained. This transformation constitutes a new example of Huntzsch synthesis of 1,4‐dihydropyridines [62] and has to involve a nucleophilic substitution of 48 at C‐3 [57b]. This means that 48 is acting here as an enamine compound (Scheme ) [57b].…”

Section: Discussionmentioning

confidence: 99%

“…A plausible reaction mechanism involves C‐3‐alkylation, ethanol elimination, Michael addition of a second molecule of 55 and cyclization with elimination of ammonia to give 96 as illustrated in Scheme [62].…”

Section: Discussionmentioning

confidence: 99%

“…Reaction of 55 with 95 catalyzed by H 2 SO 4 afford (±)‐ cis ‐diethyl‐5,8‐dioxo‐1 H ‐2,4‐dihydronaphtho[2,3‐ d ]1,3‐oxazine‐2,4‐dicarboxylate ( 97 ) after 6 d (Scheme ) [62].…”

Section: Discussionmentioning

confidence: 99%

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Aminonaphthoquinones in heterocyclization

Aly

Ishak

Alsharari

et al. 2011

Journal of Heterocyclic Chem

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

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Aminonaphthoquinones in heterocyclization

Aly

Ishak

Alsharari

et al. 2011

Journal of Heterocyclic Chem

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ChemInform Abstract: Photolysis of 2‐Amino‐ and 2‐Methylamino‐1,4‐naphthoquinone.

et al. 1988

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Photoinduced Molecular Transformations. Part 142. One‐step syntheses of 1H‐benz[f]indole‐4,9‐diones and 1H‐indole‐4,7‐diones by a new regioselective photoaddition of 2‐amino‐1,4‐naphthoquinones and 2‐amino‐1,4‐benzoquinones with alkenes

Kobayashi

Takeuchi

Seko

et al. 1993

Helvetica Chimica Acta

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The 2,3-dihydro-l H-benz[flindole-4,9-diones 3 a 4 , h were formed in a one-step reaction in 13-82% yield by an unprecedented [3 + 21 regioselective photoaddition of 2-amino-l,4-naphthoquinone (1) with various electronrich alkenes 2 (Scheme 1, Table). The [3 + 21 photoadducts derived from 1 with vinyl ethers and vinyl acetate gave lH-benz[flindole-4,9-diones 412, f, i, in 33-72% yield, by spontaneous loss of the corresponding alcohol or AcOH from the resulting adducts; 4i has a kinamycin skeleton. The [3 + 21 photoaddition also took place on irradiation of the differently substituted amino-1,4-benzoquinones 6, 7, and 12 and excess alkenes 2 in benzene, giving 1H-indole-4,7-dione derivatives 13 and 14 (Scheme 3), 15a and 16 (Scheme 4), and 18 (Scheme 4 ) , respectively. The initial products in these photoadditions were proved to be hydroquinones, the air oxidation of which yielded the heterocyclic quinones; 2,3-dihydro-2-rnethoxy-2-methyl-5-phenyl-1 H-indole-1,4,7-triyl triacetate (19) was isolated after treatment of the crude photoaddition mixture obtained from 2-amino-5-phenyl-1,4-benzoquinone (7) and 2-methoxyprop-1-ene (20 with Ac,O and pyridine under N,. A pathway leading to the annelated hydroquinones involving ionic intermediates arising from an electron transfer in these photoadditions is proposed (Scheme 5 ) .In previous papers, we reported on a one-step synthesis of 2,3-dihydronaphtho- In this paper, we describe the full details concerning this work [4]. We also describe an extention of the [3 + 21 photoaddition to the one-step formation of lH-indole-4,7-diones from 2-amino-1 ,Cbenzoquinone and various alkenes.') Part 141: [l].' )

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Photolysis of 2-amino- and 2-methylamino-1,4-naphthoquinone

Cited by 11 publications

References 5 publications

Aminonaphthoquinones in heterocyclization

Aminonaphthoquinones in heterocyclization

ChemInform Abstract: Photolysis of 2‐Amino‐ and 2‐Methylamino‐1,4‐naphthoquinone.

Photoinduced Molecular Transformations. Part 142. One‐step syntheses of 1H‐benz[f]indole‐4,9‐diones and 1H‐indole‐4,7‐diones by a new regioselective photoaddition of 2‐amino‐1,4‐naphthoquinones and 2‐amino‐1,4‐benzoquinones with alkenes

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