A Novel Method for the Synthesis of Furo-imidazo[3.3.3]propellanes from Thiocarbonohydrazides

Hassan, Alaa A.; Mohamed, Shaaban K.; Abdel-Latif, Mohamed E; Mostafa, Sara M.; Abdel‐Aziz, Mohamed; Mague, Joel T.; Akkurt, Mehmet

doi:10.1055/s-0035-1560828

Cited by 11 publications

(8 citation statements)

References 21 publications

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“…Hassan et al reported that reaction of equimolar amounts of the thiocarbonohydrazide derivative 155 and the inden‐2‐ylidenepropanedinitrile 151 in tetrahydrofuran, with admission of air and stirring at room temperature, led to the generation of an orange‐colored mixture, which quickly turned reddish‐brown. Continued stirring of the mixture resulted in the precipitation of fine colorless crystals of furo‐imidazo[3.3.3]propellane 158 via the cycloaddition intermediate 157 (Scheme ) .…”

Section: Reactions Of Bis‐thioureasmentioning

confidence: 99%

Bis‐thiourea Derivatives and Their Utility in Synthesis of Mono‐heterocyclic, Bis‐heterocyclic, and Fused Heterocyclic Systems

Dawood

2019

Journal of Heterocyclic Chem

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Bis‐thiourea derivatives have distinguished synthetic potentialities. They are interesting substrates for construction of various classes of heterocycles, such as thiazoles, thiadiazoles, imidazoles, bis‐thiazoles, bis‐thiadiazoles, and fused heterocyclic systems. The current review is concerned on disclosing the synthetic and research applications of bis‐thioureas that were reported in the literature during the last decade.

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Section: Reactions Of Bis‐thioureasmentioning

confidence: 99%

Bis‐thiourea Derivatives and Their Utility in Synthesis of Mono‐heterocyclic, Bis‐heterocyclic, and Fused Heterocyclic Systems

Dawood

2019

Journal of Heterocyclic Chem

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“…Interestingly, furo‐imidazo[3.3.3] propellanes 45a – d were synthesized in 85–92% yields by the reactions of 35a – d with 2‐(1,3‐dioxo‐2,3‐dihydro‐1 H ‐inden‐2‐ylidene)propanedinitrile (CNIND, 44 ) in tetrahydrofuran (THF) as a solvent (Scheme ) .…”

Section: Thiocarbohydrazidesmentioning

confidence: 99%

An Update of the Use of Thiocarbohydrazides and Thiosemicarbazides in the Preparation of Heterocycles and Their Biological Importance

Aly

Hassan

AbdEl‐latief

2018

Journal of Heterocyclic Chem

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The inherent reactivity of thiocarbohydrazides and thiosemicarbazides makes them valuable as building blocks for the synthesis of other heterocyclic motifs. This review article discusses the recent applications of classes of compounds in syntheses of five‐membered to seven‐membered heterocycles of biological activities and remarkable number of metal complexes. Many previous reviews dealt with the reactivity of either thiosemicarbazides or thiocarbohydrazides. However, a large number of publications have recently dealt with the reactivity of thiosemicarbazides and thiocarbohydrazides. Consequently, we have found that it is of importance to shed new light on these interesting molecules.

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“…In fact, propellane derivatives are found in many biologically active compounds and natural products . Hassan and co‐workers synthesized novel furo‐imidazo[3,3,3]propellanes 63 viareactions of thiocarbonohydrazides 62 with DCID 61 at room temperature in tetrahydrofuran . The reaction proceeded by the initial attack of NH group of 62 on the electrophilic C=C of 61 to form intermediate A .…”

Section: Introductionmentioning

confidence: 99%

Ninhydrin Adducts as Valid Synthon in Organic Synthesis: A Review

Das¹,

Dutta

2020

ChemistrySelect

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Ninhydrin (1,2,3‐indanetrione hydrate) is a powerful electrophile having enormousapplications in organic and bio‐organic sciences. In the last few years, reactivity of various ninhydrin adducts have been exploited extensively for the development of diverse organic scaffolds. The present review focuses on the applications of readily accessible ninhydrin adducts as building block towards the synthesis of a variety of compounds including N‐inserted compounds, spiro‐heterocycles, medium ring compounds, polycyclic molecules, propellanes, cycloadducts, allylic anions, axially chiral molecules etc. Interestingly, some of the compounds have profound biological activities and a few display important photophysical properties. Most of the reactions described here are simple and carried out with easily available starting materials under green conditions.

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A Novel Method for the Synthesis of Furo-imidazo[3.3.3]propellanes from Thiocarbonohydrazides

Abstract: The Table of contents Title, author's name, address and table of contents S1 Crystallographic Data for Compound 5a S2-S7 Crystallographic Data for Compound 5c S8-S10 Table 10. Hydrogen-bond geometry (Å, º) of 5c

Cited by 11 publications

References 21 publications

Bis‐thiourea Derivatives and Their Utility in Synthesis of Mono‐heterocyclic, Bis‐heterocyclic, and Fused Heterocyclic Systems

Bis‐thiourea Derivatives and Their Utility in Synthesis of Mono‐heterocyclic, Bis‐heterocyclic, and Fused Heterocyclic Systems

An Update of the Use of Thiocarbohydrazides and Thiosemicarbazides in the Preparation of Heterocycles and Their Biological Importance

Ninhydrin Adducts as Valid Synthon in Organic Synthesis: A Review

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