Michael additions of 1,2-dihydro-3H-indol-3-ones and some reactions of Michael adducts with ammonium acetate

Kawasaki, Tomomi; Tang, Chen-Ying; Nakanishi, H.; Hirai, Shuiti; Ohshita, Tomohisa; Tanizawa, Mami; Himori, Motomu; Satoh, Hiroshi; Sakamoto, Masanori; Miura, Keiko; Nakano, Fumio

doi:10.1039/a807895e

Cited by 10 publications

(3 citation statements)

References 10 publications

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“…Treatment of 1 with dimethyl acetylenedicarboxylate gives the conjugate addition product 12 (41%) which adopts the tautomer shown exclusively. The analogous tautomer is obtained when dimethyl acetylenedicarboxylate is reacted with indoxyl, 14 but an alternative tautomer is formed when dimethyl acetylenedicarboxylate is reacted with 1-substituted 3-hydroxypyrroles. 15…”

Section: Methodsmentioning

confidence: 97%

3-Hydroxy-1H-pyrrole

Hill¹,

Imam²,

McNab³

et al. 2009

Synthesis

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Flash vacuum pyrolysis (FVP) of tert-butyl {[(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl]amino}acetate at 600 °C gives the unstable 3-hydroxy-1H-pyrrole in ca. 55% yield as the only significant product. It exists as the enol tautomer in dimethyl sulfoxide solution, and predominantly as the keto tautomer in water. 3-Hydroxy-1H-pyrrole reacts readily with mild electrophiles, exclusively at the 2-position. FVP of the product obtained from one such reaction with methoxymethylene-substituted Meldrum's acid gives pyrano[3,2-b]pyrrol-5(1H)-one in 77% yield.

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Section: Methodsmentioning

confidence: 97%

3-Hydroxy-1H-pyrrole

Hill¹,

Imam²,

McNab³

et al. 2009

Synthesis

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“…The tandem `Michael addition ± aldol reaction' and `Michael addition ± aldol reaction ± Michael reaction' sequences have been described. 48 Dimethyl fumarate 107 reacted with heterocyclic ketone 108 in the presence of Et 3 N to give the expected Michael adduct 109 (the yield was 38%) along with pyrrolo[1,2-a]indoles 110 (16%) and 111 (3%) (Scheme 4). Heating of the individual compound 109 with Et 3 N afforded the product 110 the formation of which is attributable to spontaneous intramolecular cyclisation of the diester 109 followed by elimination of MeOH.…”

Section: Tandem `Michael Reaction ± Aldol Reaction' Sequencementioning

confidence: 99%

Tandem transformations initiated and determined by the Michael reaction

Gorobets¹,

Мифтахов²,

Валеев³

2000

Russ. Chem. Rev.

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“…A number of representatives of these series displayed antituberculosis, monoamine oxidase inhibiting, antiviral, antihypoxic, and hepatoprotective activities some of which may be attributable to monoamine oxidase inhibition. It is noteworthy that acetylindoxyl derivatives were also used for the synthesis of such hetero [b]fused indoles as alkaloids ellipticine [11] and quindoline [12] and other fused indoles [13][14][15]. It is noteworthy that acetylindoxyl derivatives were also used for the synthesis of such hetero [b]fused indoles as alkaloids ellipticine [11] and quindoline [12] and other fused indoles [13][14][15].…”

Section: Introductionmentioning

confidence: 99%

A Versatile Approach for the Synthesis of 8H‐Thieno[2,3‐b]indoles and N‐[2‐(2‐N‐(R₁,R₂)‐2‐Thioxoacetyl)‐phenyl]acetamides from 1‐Acetyl‐1,2‐dihydro‐3H‐indol‐3‐one (Acetylindoxyl) and Its Derivatives: A Novel Synthesis of Intermediate (1‐Acetyl‐1H‐indol‐3‐yl)malononitrile/cyanoacetates

Velezheva

Lepyoshkin

Turchin

et al. 2013

Journal of Heterocyclic Chem

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We report on two approaches for the synthesis of new 2‐amino‐3‐cyano/alkoxycarbonyl‐8H‐thieno[2,3‐b]indoles 5 and another one for the synthesis of 2‐N,N‐dialkylamino‐3‐cyano/aryl‐8H‐thieno[2,3‐b]indoles 16, based either on acetylindoxyl 1 and (1‐acetyl‐1H‐indol‐3‐yl)malononitrile/cyanoacetates 14 or 2‐bromoacetylindoxyl 2 transformations. A new, simple, rapid, and efficient method for the synthesis of valuable key intermediate malononitrile/cyanoacetates 14 based on acetylindoxyl 1 condensation with malononitrile or cyanoacetates in the presence of triethylamine has been developed. A number of synthetic procedures for the preparation of thioacetamides 6, 1‐acetylthioisatin 8, and 2,2‐disubstituted indoxyls 13 have been elaborated during the synthesis of thieno[2,3‐b]indoles. Thioacetamides 6 have been shown as novel agents active against Mycobacterium tuberculosis H37Rv, the cause of tuberculosis, with minimal inhibitory concentration values ranging between 5 and 21 μg/mL.

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Michael additions of 1,2-dihydro-3H-indol-3-ones and some reactions of Michael adducts with ammonium acetate

Cited by 10 publications

References 10 publications

3-Hydroxy-1H-pyrrole

3-Hydroxy-1H-pyrrole

Tandem transformations initiated and determined by the Michael reaction

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