Angular heterocycles. A convenient synthesis of 6‐N‐(acetylanilino)‐5H‐benzo[a]phenothiazin‐5‐one, 6‐N‐(acetylanilino)‐5H‐benzo[a]phenoxazin‐5‐ones and their derivatives

Agarwal, N. L.; Ghosh, Swapankumar; Tripathi, Anil Kumar; Atal, C.K.

doi:10.1002/jhet.5570210248

Cited by 8 publications

(2 citation statements)

References 13 publications

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“…У літературі описано чимало способів отримання гетероциклічних сполук з атомами нітрогену в циклі (хіноксалінів, феназинів, фенотіазинів, феноксазинів), в основі яких лежить взаємодія 1,4-та 1,2-хінонів з аліфатичними та ароматичними діамінами та їх похідними [2][3][4][5][6][7]. З огляду на це, ми дослідили взаємодію синтезованих арилнафтохінонів 1-7 з деякими біфункційними амінами.…”

Section: результати досліджень та їх обговоренняunclassified

Arylnaphthoquinones. 7. Synthesis of angular heterocycles from 2-aryl-1,4-naphthoquinones

Martyak¹,

Rohovyk²,

Nestoruk³

2019

Visnyk Lviv Univ. Ser. Chem.

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Реакцією арендіазонієвих солей з 1,4-нафтохіноном в умовах купрумкаталізу синтезовано 2-арил-1,4-нафтохінони. Взаємодією арилнафтохінонів з етан-1,2-діаміном отримано конденсовані гетероцикли -похідні 5-арилбензо[f]хіноксаліну. Реакцією 2-арил-1,4нафтохінонів з 2-амінобензентіолом, 2-амінофенолом та бензен-1,2-діаміном одержано ангулярні гетероциклічні системи -6-арилбензо[a]фено-тіазини, 6-арилбензо[a]феноксазини та 6-арилбензо[a]феназини, відповідно. Ключові слова: 2-арил-1,4-нафтохінони, бензо[f]хіноксаліни, бензо[a]фено-тіазини, бензо[a]феноксазини, бензо[a]феназини.

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Section: результати досліджень та їх обговоренняunclassified

Arylnaphthoquinones. 7. Synthesis of angular heterocycles from 2-aryl-1,4-naphthoquinones

Martyak¹,

Rohovyk²,

Nestoruk³

2019

Visnyk Lviv Univ. Ser. Chem.

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“…To enable a second substitution to take place, therefore, an electron-withdrawing effect must be imposed on the quinonic ring. Among the several methods developed, [13][14][15][16] we chose to apply N-acylation of the monoaminoquinones. Reaction of 2 with acetic anhydride, in the presence of sulfuric acid, afforded the acylated derivatives 3 in good yields.…”

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Synthesis of Eight-, Nine-, and Ten-Membered, Nitrogen-Containing Quinone-Fused Heterocycles

Yerushalmi¹,

Lemcoff²,

Bittner³

2007

Synthesis

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A series of allylamino-, diallylamino-, homoallylaminoand bishomoallylamino naphthoquinones were synthesized. Ruthenium-mediated ring-closing metathesis (RCM) efficiently converted these substrates into novel eight-, nine-, and ten-membered quinone-fused heterocycles. Hydro-derivatives of diazacine, diazonine, and diazecine were isolated and characterized.Quinones and their derivatives are important biological compounds, which participate in most crucial bioprocesses in living cells. They are found in higher plants, fungi, bacteria, and throughout the animal kingdom. Their central role in biosynthetic processes involves electron transport in cellular respiration (ubiquinones) and photosynthesis (plastoquinones). Numerous natural products, such as rifamycins, 2 damavaricins 3 and streptovaricins, 4 contain the aminonaphthoquinone moiety in their structure 1 and derivatives of these compounds have been synthesized and used as antitrypanosomal, 5 antimalarial, 6 antitumor 7 and antineoplastic 8 agents. They have also found use in color chemistry, hair dying, 9 and as photostabilizers. 10 As several of the highly active antibiotics contain quinones embedded in a macrocyclic structure and, in several cases, the quinone is bridged to the cyclic part via an NH group, it became of interest to prepare and study such model compounds.Our strategy was to first attach two aliphatic chains via NH bridges to a quinonic compound and, subsequently, to join these chains to form a medium-sized ring. The availability and functional group tolerance of second-generation Grubbs' catalysts made it an attractive candidate for the preparation of such macrocyclic systems via alkene ring-closing metathesis. 11 In this paper we describe our initial studies on attaching allylamine and homoallylamine to a naphthoquinone core and the formation of novel naphthoquinone hydro-derivatives of diazacine, diazonine and diazecine.It is known that aliphatic as well as aryl amines of enhanced nucleophilicity react with 2,3-dichloro-1,4-naphthoquinone (1), substituting only one chlorine atom, yielding the vinylogous amides: 2-alkyl (aryl) amino-3-chloro-1,4-naphthoquinones. 12 Indeed, allylamine and homoallylamine both smoothly substituted one chlorine atom of quinone 1, producing the monosubstituted derivatives 2a and 2b in high yields (Scheme 1). Such substitutions induce electronic enrichment of the quinone system and inhibits the replacement of the second chlorine atom. To enable a second substitution to take place, therefore, an electron-withdrawing effect must be imposed on the quinonic ring. Among the several methods developed, 13-16 we chose to apply N-acylation of the monoaminoquinones. Reaction of 2 with acetic anhydride, in the presence of sulfuric acid, afforded the acylated derivatives 3 in good yields. The substitution of the second chlorine atom thus became possible and the 2,3-diallylamino-(4a), 2-allylamino 3-homoallylamino-(4b), 3-allylamino 2-homoallylamino-(4c) and 2,3-bishomoallylamino (4d) derivatives could be obtained.The 1 H NMR sp...

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ChemInform Abstract: ANGULAR HETEROCYCLES. A CONVENIENT SYNTHESIS OF 6‐N‐(ACETYLANILINO)‐5H‐BENZO(A)PHENOTHIAZIN‐5‐ONE, 6‐N‐(ACETYLANILINO)‐5H‐BENZO(A)PHENOXAZIN‐5‐ONES AND THEIR DERIVATIVES

Agarwal¹,

GHOSH²,

Tripathi³

et al. 1984

Chemischer Informationsdienst

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Angular heterocycles. A convenient synthesis of 6‐N‐(acetylanilino)‐5H‐benzo[a]phenothiazin‐5‐one, 6‐N‐(acetylanilino)‐5H‐benzo[a]phenoxazin‐5‐ones and their derivatives

Cited by 8 publications

References 13 publications

Arylnaphthoquinones. 7. Synthesis of angular heterocycles from 2-aryl-1,4-naphthoquinones

Arylnaphthoquinones. 7. Synthesis of angular heterocycles from 2-aryl-1,4-naphthoquinones

Synthesis of Eight-, Nine-, and Ten-Membered, Nitrogen-Containing Quinone-Fused Heterocycles

ChemInform Abstract: ANGULAR HETEROCYCLES. A CONVENIENT SYNTHESIS OF 6‐N‐(ACETYLANILINO)‐5H‐BENZO(A)PHENOTHIAZIN‐5‐ONE, 6‐N‐(ACETYLANILINO)‐5H‐BENZO(A)PHENOXAZIN‐5‐ONES AND THEIR DERIVATIVES

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