The syntheses of some novel 2-substituted phenylazo-1,3-indandiones

Hocaoglu, N.; Uyar, Tahsin; Türker, Lemi

doi:10.1016/0143-7208(90)85011-c

Cited by 10 publications

(3 citation statements)

References 13 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The structures of 8a-e were also confirmed by their alternative synthesis. Thus, reaction of 7a-e [20,21], prepared by coupling of 1,3-indanedione 2 with aryl diazonium chloride, with malononitrile in boiling ethanol in the presence of piperidine gave 8a-e (Scheme 2). Boiling compound 8a in acetic anhydride gave the corresponding N-acetylimino derivative 9.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of some new Indeno[1,2-e]pyrazolo[5,1-c]-1,2,4-triazin-6-one and Indeno[2,1-c]pyridazine-4-carbonitrile Derivatives

Abunada¹,

Hassaneen²

2010

View full text Add to dashboard Cite

Diazonium chlorides of 5-amino-3-methypyrazole 1a and 5-amino-4-phenylpyrazole 1b coupled with 1,3-indanedione 2 and led to the formation of acyclic hydrazone 3a and a cyclic product indenopyrazolotriazine 4b respectively. Cyclization of the hydrazone 3a by boiling in acetic acid afforded the corresponding 4a. The hydrazone 3a reacted with malononitrile in boiling ethanol in the presence of piperidine and gave indeno[2,1-c]pyridazine-4-carbonitrile derivatives 5a,b. Also, coupling of 6 with aryl diazonium chlorides gave the corresponding indenopyridazine derivatives 8a-e. Acetylation, benzoylation and hydrolysis of compound 8a afforded the corresponding substitution products 10-12, respectively. The structures of the newly synthesized compounds were established on the basis of chemical and spectral evidences

show abstract

Section: Resultsmentioning

confidence: 99%

Synthesis of some new Indeno[1,2-e]pyrazolo[5,1-c]-1,2,4-triazin-6-one and Indeno[2,1-c]pyridazine-4-carbonitrile Derivatives

Abunada¹,

Hassaneen²

2010

View full text Add to dashboard Cite

show abstract

“…Crystal structure of pindone was determined [7]. On the other hand, the tautomerism in indandiones has attacked attention especially in the past [8][9][10][11].…”

Section: Introductionmentioning

confidence: 99%

Tautomerism in Pindone – A DFT Study

Türker

2019

EJCS

Self Cite

View full text Add to dashboard Cite

Pindone is a rodenticide having three keto groups in its structure. Presently, 1,3-type keto-enol tautomerism of pindone has been studied within the constraints of density functional theory at the level of B3LYP/6-311++G(d,p). Various structural and quantum chemical properties of these tautomers have been obtained, compared and discussed. Endocyclic and exocyclic enol forms of pindone are accompanied by dipole moment vectors having opposite directions. The endocyclic enol structure is found to be more stable than the exocyclic enol and pindone. IR and UV-VIS spectra are obtained. NICS(0) values are calculated to visualize the effect of tautomerism on the local aromaticity of the structures considered.

show abstract

“…Crystal structure of pindone was determined [7]. On the other hand, the tautomerism in indandiones has attracted attention especially in the past [8][9][10][11].…”

mentioning

confidence: 99%

Interaction of Pindone and its Tautomers with Calcium Dication – A DFT Study

Türker

2020

EJCS

Self Cite

View full text Add to dashboard Cite

Calcium dication has an important role at various stages of blood coagulation mechanism. On the other hand, pindone is an important anticoagulant rodenticide which undergoes 1,3-type proton tautomerism to yield two enolic isomers of pindone. Although, the anticoagulant mode of action of pindone is attributed to blocking of a liver enzyme responsible for the recycling of vitamin K, nothing is known about whether the interaction of it with calcium dication has some role as well. In the present study, the interactions of pindone and its tautomers with Ca++ have been investigated within the restrictions of density functional theory at the level of B3LYP/6-311++G(d,p). It has been found that Ca++ highly affects pindone and its tautomers in many respects at the molecular level, hence their anticoagulation effect should vary.

show abstract

The syntheses of some novel 2-substituted phenylazo-1,3-indandiones

Cited by 10 publications

References 13 publications

Synthesis of some new Indeno[1,2-e]pyrazolo[5,1-c]-1,2,4-triazin-6-one and Indeno[2,1-c]pyridazine-4-carbonitrile Derivatives

Synthesis of some new Indeno[1,2-e]pyrazolo[5,1-c]-1,2,4-triazin-6-one and Indeno[2,1-c]pyridazine-4-carbonitrile Derivatives

Tautomerism in Pindone – A DFT Study

Interaction of Pindone and its Tautomers with Calcium Dication – A DFT Study

Contact Info

Product

Resources

About