Preparative Synthesis of 7-Carboxy-2-R-isoindol-1-ones

Varlamov, A. V.; Boltukhina, Ekaterina V.; Zubkov, Fedor I.; Sidorenko, N. V.; Chernyshev, A. I.; Grudinin, D. G.

doi:10.1023/b:cohc.0000023763.75894.63

Cited by 21 publications

(9 citation statements)

References 10 publications

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“…Recrystallization from 2-propanol-DMF gave the corresponding acids as colorless crystals: 4b in 45% yield, 4c in 62% yield, and 4d in 40% yield. The physicochemical characteristics and spectral data for acids 4b,c were identical to the results reported in our previous work [20].…”

Section: -Oxo-2-phenyl-23-dihydro-1h-isoindole-4-carboxylic Acid (4supporting

confidence: 84%

“…The addition takes place through the intermediate formation of the maleic acid furfurylamide 2' and subsequent exo- [4+2] cycloaddition of the unsaturated fragment to a furan ring [20]. The cycloaddition to furfurylamines 1b-d at room temperature proceeds nonselectively at both furan fragments to give a mixture of isomeric N-furfuryloxoepoxyisoindolonecarboxylic acids 2b-dA and 2b-dB.…”

mentioning

confidence: 99%

“…Attempts to effect aromatization of the 7-oxa-bicyclo[2.2.1]heptene fragment by the action of strong mineral acids such as HCl, H 3 PO 4 , and H 2 SO 4 at various concentrations [20] were unsuccessful. Acid 2e is aromatized at room temperature by boron trifluoride etherate in acetic anhydride to give isoindolone 4a.…”

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confidence: 99%

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Cycloaddition of furfurylamines to maleic anhydride and its substituted derivatives

Zaytsev

Mikhailova

Airiyan

et al. 2012

Chem Heterocycl Comp

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Functionally substituted epoxyisoindolones hold interest for use in organic synthesis. Pseudo-sugars annelated with azaheterocycles [1][2][3], and various condensed heterocyclic compounds containing an isoindole fragment may be obtained on the basis of these compounds [4][5][6][7][8][9][10]. A recently developed method for the synthesis of isoindol-1-ones holds considerable promise in this regard. This method is based on the acylation of N-aryl-or N-alkylfurfurylamines by unsaturated acid derivatives with subsequent intramolecular [4+2] cycloaddition of the resultant unsaturated amides [11][12][13][14][15][16][17][18][19].The development of this approach is an elaboration of the two-step preparative method for the synthesis of 7-carboxy-2-R-isoindol-1-ones [20] based on [4+2] cycloaddition of maleic anhydride to N-substituted furfurylamines. We studied the scope of this reaction and showed the effect of the substituent at the furfurylamine nitrogen atom on the cycloaddition. Conditions were found for the aromatization of the oxabicycloheptene fragment to give 7-carboxyphthalimidines [21].In the present work, we have studied the regio-and stereoselectivity of the cycloaddition of maleic, citraconic, dibromomaleic, and dichloromaleic anhydrides to difurfurylamines as well as to phenyl-and benzylfurfurylamines. An attempt was made to evaluate the effect of substituents in the oxabicycloheptene fragment on the capacity of the Diels-Alder adducts to undergo aromatization.Starting furfurylamines 1a-h were obtained as light, mobile oils by the reduction of the corresponding Schiff bases using sodium borohydride in ethanol.

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Section: -Oxo-2-phenyl-23-dihydro-1h-isoindole-4-carboxylic Acid (4supporting

confidence: 84%

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confidence: 99%

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Cycloaddition of furfurylamines to maleic anhydride and its substituted derivatives

Zaytsev

Mikhailova

Airiyan

et al. 2012

Chem Heterocycl Comp

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“…The 1 (9), 208 (32), 206 (100), 204 (9), 138 (9), 135 (7), 117 (5), 111 (7), 99 (14), 91 (8) The IR spectra were recorded on a UR 20 instrument in KBr pellets for solid compounds and in films for oils.…”

Section: Methodsmentioning

confidence: 99%

Study of regioselectivity of intramolecular cyclization of N-(m-R-phenyl)- and N-(α-naphthyl)-2-allyl(methallyl)-6-carboxy-4-oxo-3-aza-10-oxatricyclo[5.2.1.01,5]dec-8-enes

et al. 2004

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Regioselectivity of the intramolecular electrophilic substitution in a series of N (m R phenyl) and N (α naphthyl) 2 allyl(methallyl) 6 carboxy 4 oxo 3 aza 10 oxatri cyclo[5.2.1.0 1,5 ]dec 8 enes in reactions with phosphoric acid was studied. The reactions of N (m R phenyl) substituted derivatives proceed nonregioselectively to form mixtures of 2 R and 4 R substituted isoindolo[2,1 a]quinolines, whereas the reactions of N (α naph thyl) substituted derivatives occur regioselectively at the β position of the naphthyl fragment.

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“…In a H 3 PO 4 medium at 85°C, we observed the aromatization of oxabicycloheptane fragment [14] in epoxyisoindoloquinolin carboxylic acids 6aA , 6mB , 7aB , 11aB , as well as in epoxyisoindoloquinolines 10aB , 10iB , 10mB , 15 , 16 . It is interesting to note that the action of hot phosphoric acid on isoindoloquinolines 20a , 20b , 20c , 20e , 20f , 20g , 20h , 20i does not lead to N ‐amide substituent ( R 4 ) elimination, which was observed before for analogous structures by the action of BF 3 × Et 2 O at room temperature [8].…”

Section: Introductionmentioning

confidence: 99%

5‐Amido‐ and 5‐Amino‐Substituted Epoxyisoindolo[2,1‐a]tetrahydroquinolines and 10‐Carboxylic Acids: Their Synthesis and Reactivity

Zaytsev

Zubkov

Toze

et al. 2013

Journal of Heterocyclic Chem

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The interactions between 4‐R‐substituted 2‐furyl‐1,2,3,4‐tetrahydroquinolines (synthesized by the Povarov reaction) and a number of alkenes have been investigated. Maleic, dibromomaleic, dichloromaleic, and citraconic anhydrides, as well as acryloyl, methacryloyl, crotonyl, and cynnamoyl chlorides were used as alkene components. It was shown that the initial N‐acylation of the tetrahydroquinolines was followed by a spontaneous [4+2]‐cycloaddition of an N‐acryloyl substituent to the furan ring. It was established that the intramolecular Diels–Alder reaction of furans is reversible, occurs stereoselectively as exo‐addition, and led to target epoxyisoindolo[2,1‐a]tetrahydroquinolines with moderate yields. Oxidation and aromatization of the synthesized products were carried out.

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Preparative Synthesis of 7-Carboxy-2-R-isoindol-1-ones

Cited by 21 publications

References 10 publications

Cycloaddition of furfurylamines to maleic anhydride and its substituted derivatives

Cycloaddition of furfurylamines to maleic anhydride and its substituted derivatives

Study of regioselectivity of intramolecular cyclization of N-(m-R-phenyl)- and N-(α-naphthyl)-2-allyl(methallyl)-6-carboxy-4-oxo-3-aza-10-oxatricyclo[5.2.1.01,5]dec-8-enes

5‐Amido‐ and 5‐Amino‐Substituted Epoxyisoindolo[2,1‐a]tetrahydroquinolines and 10‐Carboxylic Acids: Their Synthesis and Reactivity

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