Abstract:The 2‐phenylimino‐1,3‐thiazolidin‐4‐one 2 was obtained by thermal cyclization of 4‐amino‐5‐phen‐yl‐3, 5‐thiaaza‐4‐pentenoic acid 1 using DCC as dehydration agent. Treatment of 2‐phenylimino‐1,3‐thiazolidin‐4‐one 2 with various hydrazonoyl halides 3 (nitrilimines 4 precursor) yielded 6‐aryl‐9‐phenyl‐8‐substituted‐1,4,6,7,9‐thiatetrazaspiro‐[4.4]non‐7‐en‐3‐ones 5a‐1. Both analytical and spectroscopic data of all the synthesized compounds are in full agreement with the proposed structures.
“…Earlier, it was reported that the cycloaddition of nitrile imines to the C=N bond of 2-iminothiazolidine-4-ones makes it possible to obtain a spiro-joined product containing the unaffected thiazolidine cycle [ 26 ] ( Scheme 6 a). Meanwhile, the reactions of diphenyl nitrile imine with 5-arylidene-substituted 2-iminothiazolidine-4-one resulted in the formation of a product of the sequential addition of two dipole molecules along both exocyclic double bonds C=N and C=S, which were formed as a result of the rearrangement of the intermediate spiro compound [ 27 ] ( Scheme 6 b).…”
Section: Resultsmentioning
confidence: 99%
“… Reactions of nitrilimines with 2-iminothiazolidine-4-one ( a ) and its 5-arylidene derivative ( b ) [ 26 , 27 ]. …”
Section: Figures Schemes and Tablesmentioning
confidence: 99%
“…The use of the latter enabled the Scheme 6. Reactions of nitrilimines with 2-iminothiazolidine-4-one (a) and its 5-arylidene derivative (b) [26,27].…”
Section: 3-dipolar Cycloaddition Of Nitrile Imines To 2-thioxoimidazo...mentioning
confidence: 99%
“…Meanwhile, the reactions of diphenyl nitrile imine with 5-arylidene-substituted 2-iminothiazolidine-4-one resulted in the formation of a product of the sequential addition of two dipole molecules along both exocyclic double bonds C=N and C=S, which were formed as a result of the rearrangement of the intermediate spiro compound[27] (Scheme 6b).Scheme 5. The proposed products of the 1-allyl-2-thioxoimidazolidine-4,5-dione 1f and hydrazonoyl chloride 3b reactions.Earlier, it was reported that the cycloaddition of nitrile imines to the C=N bond of 2-iminothiazolidine-4-ones makes it possible to obtain a spiro-joined product containing the unaffected thiazolidine cycle[26] (Scheme 6a). Meanwhile, the reactions of diphenyl nitrile imine with 5-arylidene-substituted 2-iminothiazolidine-4-one resulted in the formation of a product of the sequential addition of two dipole molecules along both exocyclic double bonds C=N and C=S, which were formed as a result of the rearrangement of the intermediate spiro compound[27] (Scheme 6b).…”
Approximately 1,3-Dipolar cycloaddition of imidazolidine derivatives containing exocyclic double bonds is a convenient method of creating spiro-conjugated molecules with promising anticancer activity. In this work, the derivatives of parabanic acid (2-thioxoimidazolidine-4,5-diones and 5-aryliminoimidazolidine-2,4-diones) were first investigated as dipolarophiles in the reactions with nitrile imines. The generation of nitrile imines was carried out either by the addition of tertiary amine to hydrazonoyl chlorides «drop by drop» or using the recently proposed diffusion mixing technique, which led to ~5–15% increases in target compound yields. It was found that the addition of nitrile imines to C=S or C=N exocyclic double bonds led to 1,2,4-thiazolines or triazolines and occurred regioselectively in accordance with the ratio of FMO coefficients of reactants. The yield of the resulting spiro-compound depended on the presence of alkyl substituents in the nitrile imine structure and was significantly decreased in reactions with imines with strong electron donor or electron-withdrawing groups. Some of the obtained compounds showed reasonable in vitro cytotoxicity. IC50 values were calculated for HCT116 (colon cancer) cells using the MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) test.
“…Earlier, it was reported that the cycloaddition of nitrile imines to the C=N bond of 2-iminothiazolidine-4-ones makes it possible to obtain a spiro-joined product containing the unaffected thiazolidine cycle [ 26 ] ( Scheme 6 a). Meanwhile, the reactions of diphenyl nitrile imine with 5-arylidene-substituted 2-iminothiazolidine-4-one resulted in the formation of a product of the sequential addition of two dipole molecules along both exocyclic double bonds C=N and C=S, which were formed as a result of the rearrangement of the intermediate spiro compound [ 27 ] ( Scheme 6 b).…”
Section: Resultsmentioning
confidence: 99%
“… Reactions of nitrilimines with 2-iminothiazolidine-4-one ( a ) and its 5-arylidene derivative ( b ) [ 26 , 27 ]. …”
Section: Figures Schemes and Tablesmentioning
confidence: 99%
“…The use of the latter enabled the Scheme 6. Reactions of nitrilimines with 2-iminothiazolidine-4-one (a) and its 5-arylidene derivative (b) [26,27].…”
Section: 3-dipolar Cycloaddition Of Nitrile Imines To 2-thioxoimidazo...mentioning
confidence: 99%
“…Meanwhile, the reactions of diphenyl nitrile imine with 5-arylidene-substituted 2-iminothiazolidine-4-one resulted in the formation of a product of the sequential addition of two dipole molecules along both exocyclic double bonds C=N and C=S, which were formed as a result of the rearrangement of the intermediate spiro compound[27] (Scheme 6b).Scheme 5. The proposed products of the 1-allyl-2-thioxoimidazolidine-4,5-dione 1f and hydrazonoyl chloride 3b reactions.Earlier, it was reported that the cycloaddition of nitrile imines to the C=N bond of 2-iminothiazolidine-4-ones makes it possible to obtain a spiro-joined product containing the unaffected thiazolidine cycle[26] (Scheme 6a). Meanwhile, the reactions of diphenyl nitrile imine with 5-arylidene-substituted 2-iminothiazolidine-4-one resulted in the formation of a product of the sequential addition of two dipole molecules along both exocyclic double bonds C=N and C=S, which were formed as a result of the rearrangement of the intermediate spiro compound[27] (Scheme 6b).…”
Approximately 1,3-Dipolar cycloaddition of imidazolidine derivatives containing exocyclic double bonds is a convenient method of creating spiro-conjugated molecules with promising anticancer activity. In this work, the derivatives of parabanic acid (2-thioxoimidazolidine-4,5-diones and 5-aryliminoimidazolidine-2,4-diones) were first investigated as dipolarophiles in the reactions with nitrile imines. The generation of nitrile imines was carried out either by the addition of tertiary amine to hydrazonoyl chlorides «drop by drop» or using the recently proposed diffusion mixing technique, which led to ~5–15% increases in target compound yields. It was found that the addition of nitrile imines to C=S or C=N exocyclic double bonds led to 1,2,4-thiazolines or triazolines and occurred regioselectively in accordance with the ratio of FMO coefficients of reactants. The yield of the resulting spiro-compound depended on the presence of alkyl substituents in the nitrile imine structure and was significantly decreased in reactions with imines with strong electron donor or electron-withdrawing groups. Some of the obtained compounds showed reasonable in vitro cytotoxicity. IC50 values were calculated for HCT116 (colon cancer) cells using the MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) test.
“…While in the second step, the Nitrogen atom of Schiff’s base undergoes attack by a sulfur nucleophile (thioglycolic acid) followed by intramolecular cyclization and elimination of water in the presence of DCC (N,N′-Dicyclohexylcarbodiimide). The DCC is used to accelerate the intramolecular cyclization which results in faster reaction and improved yield [32] , [33] . Scheme 1 Scheme for the synthesis of 2-( R - phenyl)-3-[(4-methylphenyl)sulfonyl]-1,3-thiazolidin-4-one derivatives 5 (a-t).…”
1,3‐Dipolar cycloaddition of the nitrilimines with the 2‐propylidene‐3‐coumaranone afforded the corresponding pyrazole derivatives. Similar reactions of nitrilimines with 3‐ethylidene‐1‐indanone furnished spiropyrazoline derivatives. The spectral data of the synthesized compounds are in full agreement with its molecular structure.
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