Sustainable alternative protocols for the multicomponent synthesis of spiro-4H-pyrans catalyzed by 4-dimethylaminopyridine

Zakeri, Masoumeh; Nasef, Mohamed Mahmoud; Abouzari‐Lotf, Ebrahim; Moharami, Arezoo; Heravi, Majid Μ.

doi:10.1016/j.jiec.2015.03.035

Cited by 37 publications

(15 citation statements)

References 38 publications

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“…22) They are also applicable to the synthesis of heterocyclic systems. 23) It is quite remarkable that many topselling pharmaceuticals containing 4-H pyran derivatives [24][25][26][27][28] which encouraged us to synthesize the 4-H pyran and 4-H pyridine derivatives through the multi-component reactions of compound 19. Thus, compound 19 underwent the MCR of malononitrile and any of benzaldehyde, 4-chlorobenzaldehyde or 4-methoxybenzaldehyde in ethanolic triethylamine solution to give the pyran derivatives 20a-c, respectively.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Novel Heterocyclic Compounds Incorporate 4,5,6,7-Tetrahydrobenzo[b]thiophene Together with Their Cytotoxic Evaluations

Abdallah

Mohareb

Khalil

et al. 2017

CHEMICAL & PHARMACEUTICAL BULLETIN

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The 2-amino-3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophene was the key starting compound used to synthesize new thiazole, pyrimidine, pyran, pyridine and thiazine derivatives. The cytotoxicity of the synthesized compounds was studied towards the three cancer cell lines namely MCF-7 (breast adenocarcinoma), NCI-H460 (non-small cell lung cancer) and SF-268 (central nervous system (CNS) cancer) in addition to the normal cell line (WI-38) using doxorubicin as the reference drug. The study showed that compounds 5, 9a, 15b, 17c, 18 and 21b were the most potent compounds. anti-leishmanial agents, 11) antioxidant activity, 12) anti-arrhythmic, serotonin antagonist and anti-anxiety activities. Key words 13)Recently we were involved through the synthesis of polyfunctional heterocyclic compounds, where the 2-cyanomethylbenzo[c] imidazole was used as the key starting compound.14) In addition, we were involved through the reaction of ethyl acetoacetate with elemental sulphur and either malononitrile or ethyl cyanoacetate gave thiophene derivatives. 15) In the present work we were concerned through exploring the reactivity of the amino group present in the 2-amino-3-cyano-4,5,6,7-tetrahydrobenzo[b] thiophene 16) towards different chemical reagents to afford a vast number of heterocyclic compounds involving tetrahydrobenzo[b]-thiophene moiety and evaluating their cytotoxicity. Results and DiscussionChemistry The reaction of the 2-amino-3-cyano-4,5,6,7-tetrahydrobenzo[b] thiophene with triethyl orthoformate in acetic acid gave the ethyl N- (3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl) formimidate 1. The analytical and spectral data of compound 1 were the tools of its structural elucidation. Compound 1 reacted with aniline to give the N-phenyl formamidine derivative 2. The elemental and spectral data of compound 2 were consistent with its proposed structure. Thus, 1 H-NMR spectrum of compound 2 showed, beside the expected signals, a singlet at 6.95 ppm δ for CH moiety, a muliplet at δ 7.27-7.90 ppm for phenyl ring and a singlet at δ 8.36 ppm for NH group. On the other hand, the reaction of compound 1 with malononitrile gave the imino-methyl malononitrile derivative 3. The analytical and spectral data of compound 3 were in agreement with its structure (see Experimental section). The reaction of compound 2-amino-3-cyano-4,5,6,7-tetrahydrobenzo[b] thiophene with phenylisothiocyanate and chloroacetone gave the thiazole derivative 5. Formation of the latter product took place through the intermediate formation of 4 followed by water elimination (Chart 1).Next we studied the possibility of compound 2-amino-3-cyano-4, 5,6,7-tetrahydrobenzo[b] thiophene to form thiourea derivative. Thus, compound 2-amino-3-cyano-4, 5,6,7-tetrahydrobenzo[b] thiophene reacted with phenyl

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Section: Resultsmentioning

confidence: 99%

Synthesis of Novel Heterocyclic Compounds Incorporate 4,5,6,7-Tetrahydrobenzo[b]thiophene Together with Their Cytotoxic Evaluations

Abdallah

Mohareb

Khalil

et al. 2017

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…33) They are also applicable to the synthesis of heterocyclic systems. 34) It is quite remarkable that many top-selling pharmaceuticals contains "4-H pyran" derivatives [35][36][37][38][39] this encouraged us to synthesis 4-H pyran derivative through the multi-component reactions of compounds 3a-c. Thus, the reaction of any of compounds 3a-c with any of benzaldehyde (6a), 4-chlorobenzaldehyde (6b) or 4-nitrobenzaldehyde (6c) and either of malononitrile (7a) or ethyl cyanoacetate (7b) gave the 5,9-dihydro-4H-thieno[2,3-f ] chromene derivatives 9a-r, respectively (Chart 2).…”

Section: Resultsmentioning

confidence: 99%

Uses of Cyclohexan-1,4-dione for the Synthesis of 2-Amino-4,5-dihydrobenzo[b]thiophen-6(7H)-one Derivatives with Anti-proliferative and Pim-1 Kinase Activities

Mohareb

Abbas

Ibrahim

2017

CHEMICAL & PHARMACEUTICAL BULLETIN

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The reaction of cyclohexan-1,4-dione with elemental sulfur and any of the 2-cyano-N-arylacetamide derivatives 2a-c gave the 2-amino-4,5-dihydrobenzo[b]thiophen-6(7H)-one derivatives 3a-c to be used in some heterocyclization reactions. The multicomponent reactions of any of compounds 3a-c with aromatic aldehydes 6a-c and either of malononitrile or ethylcyanoacetate gave the 5,9-dihydro-4H-thieno[2,3-f ]chromene derivatives 9a-r, respectively. The anti-proliferative evaluation of the newly synthesized compounds against the six cancer cell lines A549, HT-29, MKN-45, U87MG, SMMC-7721 and H460 showed that the nine compounds 3c, 5c, 9e, 9h, 9i, 9j, 9l, 9q, 11e and 13e with highest cytotoxcity. Toxicity of these compounds against shrimp larvae revealed that compounds 3c, 9j, 9q, and 13e showed no toxicity against the tested organisms. The c-Met kinase inhibition of the most potent compounds showed that compounds 9j, 9q, 10e, 12e and 13e have the highest activities. Compounds 9j, 9l, 9q and 11e showed high activity towards tyrosine kinases. Moreover, compounds 9j, 9q and 13e showed the highest inhibitor activity towards Pim-1 kinase.

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“…Multicomponent reactions are the main approaches for synthesis of special products with molecular diversity which have attracted much attention as a facial means by synthetic chemists. Therefore, the development of novel multi-component reactions is of interest for chemists [1][2][3][4][5][6][7][8].…”

Section: Introductionmentioning

confidence: 99%

Cerium (Iv) Ammonium Nitrate (Can) as a Catalyst in Water: A Simple, Proficient and Green Approach for the Synthesis of Tetrahydropyrimidine Quinolones

Geramizadegan

Mahdavinia

2017

J. Chil. Chem. Soc.

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We report here a facile, mild and efficient synthesis of functionalized tetrahydropyrimidine quinolones via one pot three-component condensation of aromatic aldehydes, N,N-dimethyl barbituricacid (barbituricacid), 4-hydroxy-1-methylquinolin-2(1H)-one and using a cerium ammonium nitrate (CAN) as a green catalyst in aqueous media-water (as a green ideal solvent) is described. The significant advantages of this protocol are short reaction time, simple work up procedure and reduced environmental impact, wide substrate scope; generally very good to excellent yields and starting materials are inexpensive and commercially available. The structures of these compounds were established on the basis of IR, 1 H NMR, 13 C NMR spectra.

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Sustainable alternative protocols for the multicomponent synthesis of spiro-4H-pyrans catalyzed by 4-dimethylaminopyridine

Cited by 37 publications

References 38 publications

Synthesis of Novel Heterocyclic Compounds Incorporate 4,5,6,7-Tetrahydrobenzo[<i>b</i>]thiophene Together with Their Cytotoxic Evaluations

Synthesis of Novel Heterocyclic Compounds Incorporate 4,5,6,7-Tetrahydrobenzo[<i>b</i>]thiophene Together with Their Cytotoxic Evaluations

Uses of Cyclohexan-1,4-dione for the Synthesis of 2-Amino-4,5-dihydrobenzo[<i>b</i>]thiophen-6(7<i>H</i>)-one Derivatives with Anti-proliferative and Pim-1 Kinase Activities

Cerium (Iv) Ammonium Nitrate (Can) as a Catalyst in Water: A Simple, Proficient and Green Approach for the Synthesis of Tetrahydropyrimidine Quinolones

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