An efficient synthesis of substituted 2-iminothiazolidin-4-one and thiadiazoloquinazolinone derivatives

Ahmadi, Sayed Ali; Saidi, Kazem; Khabazzadeh, Hojatollah

doi:10.1007/s11030-009-9124-1

Cited by 25 publications

(7 citation statements)

References 11 publications

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“…The traditional methods for thiadiazoloquinazolinone synthesis possessed certain limitations, such as reduced yields, multi-step procedures and expensive starting materials [145,146]. On water chemistry has been in the scientific community for a while but has received little attention [147].…”

Section: Fused Quinazolinonesmentioning

confidence: 99%

Microwave-assisted multicomponent reactions in heterocyclic chemistry and mechanistic aspects

Gulati¹,

John²,

Shankaraiah³

2021

Beilstein J. Org. Chem.

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Microwave-assisted (MWA) multicomponent reactions (MCRs) have successfully emerged as one of the useful tools in the synthesis of biologically relevant heterocycles. These reactions are strategically employed for the generation of a variety of heterocycles along with multiple point diversifications. Over the last few decades classical MCRs such as Ugi, Biginelli, etc. have witnessed enhanced yield and efficiency with microwave assistance. The highlights of MWA-MCRs are high yields, reduced reaction time, selectivity, atom economy and simpler purification techniques, such an approach can accelerate the drug discovery process. The present review focuses on the recent advances in MWA-MCRs and their mechanistic insights over the past decade and shed light on its advantage over the conventional approach.

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Section: Fused Quinazolinonesmentioning

confidence: 99%

Microwave-assisted multicomponent reactions in heterocyclic chemistry and mechanistic aspects

Gulati¹,

John²,

Shankaraiah³

2021

Beilstein J. Org. Chem.

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“…Ahmadi et al . successfully prepared 4‐thiazolidin‐one derivatives 272a , b via the reaction of 1‐phenyl‐3‐(pyridin‐2‐yl) thiourea 236s with DMAD 4a and DEAD 4b in tetrahydrofuran at room temperature through intermediate 271a , b (Scheme ).…”

Section: From Thioureasmentioning

confidence: 99%

Thiazolidine‐4‐ones from Thiocarbohydrazides

Hassan

Makhlouf

2018

Journal of Heterocyclic Chem

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in Wiley Online Library (wileyonlinelibrary.com).Several methods for the preparation of thiazolidin-4-ones from thiocarbohydrazides over the last 15 years are highlighted. Thiosemicarbazides, thiocarbohydrazides, thioamides, and hydrazinecarbothioamides as well as thioureas were used to obtain different substituted thiazolidinones under reaction conditions. Thiazolidinones can be synthesized either by a one-pot three-component condensation or a two-step process. Also, the mechanism of formation, regioselectivity issues, and biological activities of different thiazolidinones were discussed.

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“…Different methods for the synthesis of 1,3-thiazolidin-4-ones were reported from thiosemicarbazides [16][17][18][19][20], thiocarbohydrazides [21,22], hydrazinocarbothioamides [23,24], and thioureas [25][26][27]. Several efforts from chemists have been oriented towards reactions of thione group and dialkyl acetylenedicarboxylate for the synthesis of thiazolidinones [18,19,28].…”

Section: Introductionmentioning

confidence: 99%

Stereoselective synthesis of 2-(2,4-dinitrophenyl)hydrazono- and (2-tosylhydrazono)-4-oxo-thiazolidine derivatives and screening of their anticancer activity

et al. 2020

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Stereoselective synthesis of (Z)-methyl 2-[(Z)-3-substituted-2-(2-(2,4-dinitrophenyl)hydrazono)-4-oxothiazolidine-5-ylidine)]acetates and (Z)-methyl 2-[(Z)-3-substituted-2-(2-(tosylhydrazono)-4-oxothiazolidine-5ylidine)]acetates via the cyclization of N-substituted-2-arylhydrazinocarbothioamides with dialkyl acetylenedicarboxylates in absolute ethanol is reported. The structures were confirmed by spectroscopic data as well as single crystal X-ray analyses. The mechanism of nucleophilic addition and the role of electronic factors were discussed. The anticancer activity of the newly synthesized compounds was evaluated against a panel of 60 cell lines derived from nine different types of cancers including, leukemia, melanoma, lung, colon, CNS, ovarian, renal, prostate, and breast cancers and the results revealed that the cyclohexyl derivative has a significant broad anticancer activity especially against different leukemia and colon cancer cell lines . MCCM_Template_Vers 4

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An efficient synthesis of substituted 2-iminothiazolidin-4-one and thiadiazoloquinazolinone derivatives

Cited by 25 publications

References 11 publications

Microwave-assisted multicomponent reactions in heterocyclic chemistry and mechanistic aspects

Microwave-assisted multicomponent reactions in heterocyclic chemistry and mechanistic aspects

Thiazolidine‐4‐ones from Thiocarbohydrazides

Stereoselective synthesis of 2-(2,4-dinitrophenyl)hydrazono- and (2-tosylhydrazono)-4-oxo-thiazolidine derivatives and screening of their anticancer activity

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