ChemInform Abstract: Synthesis of Heterocyclic Compounds from Cyclohexane‐1,3‐diones

Strakov, A. Ya.; Gudrinietse, E. Yu.; Strakova, I. A.

doi:10.1002/chin.198848351

ChemInform

1988

DOI: 10.1002/chin.198848351

|View full text |Cite

ChemInform Abstract: Synthesis of Heterocyclic Compounds from Cyclohexane‐1,3‐diones

A. Ya. Strakov¹,

E. Yu. Gudrinietse²,

I. A. Strakova³

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

1998

Publication Types

Select...

Article1

Relationship

Self Cite1

Independent0

Authors

Journals

Cited by 1 publication

(1 citation statement)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…3-Methyl-l-phenyl-5-formyl-4-chloro-6,7-dihydroindazole (III) also reacts with 3-and 4-pyridinecarbamidines [2].…”

mentioning

confidence: 98%

Reactions of 3-methyl-1-(2-pyridyl)-4-chloro-5-formyl-6,7-dihydroindazole

Strakova¹,

Delyatitskaya²,

Петрова³

et al. 1998

Chem Heterocycl Compd

Self Cite

View full text Add to dashboard Cite

Earlier we modified indazoles in the reactions of 3-methyl-l-(2-pyridyl)-5-formyl-4-chloro-6,7-dihydroindazoles (I, II) with hydrazines, o-phenylenediamine, and certain C-nucleophiles [1]. In the present paper we discuss the reactions of the 3-chloroaldehydes (I-III) with guanidine, amidines, and hydroxylamine, leading to pyrazolo [5,4-h]quinazolines (IV-XII) and isoxazolo [5,4-e]indazole (XVII) respectively.When the chloroaldehydes (I, II) were boiled with guanidine carbonate, benzamidine hydrochloride, and 3-and 4-pyridinecarbamidine hydrochlorides in ethanol in the presence of sodium ethoxide, the corresponding 8-substituted 1-methyl-3-(2-pyridyl)-4,5-dihydropyrazolo[5,4-h]quinazolines (IV-IX) were obtained. 3-Methyl-l-phenyl-5-formyl-4-chloro-6,7-dihydroindazole (III) also reacts with 3-and 4-pyridinecarbamidines [2].The structure of the pyrazolo[4,5-d]quinazolines (IV-XII) is confirmed by the IR and PMR spectra (Table 1). Thus, the primary amino group of compound (IV) is characterized by the stretching vibrations at 3350 and 3150 cm -1, while the PMR spectrum contains a two-proton signal at t5 5.52 pprn.The reactions of the chloroaldehydes (I, II) with hydroxylamine hydrochloride in pyridine lead to the oximes (XIII, XIV). When boiled with acetic anhydride the chloroaldehydes (I, III) form the 4-acetoxy derivatives (XV) and (XVI). In the IR spectra of the enol acetates (XV) and (XVI) the carbonyl groups are characterized by absorption at 1774 (XV) and 1764 (XVI) cm -1. The treatment of 4-acetoxy-5-formylindazole (XV) with hydroxylamine leads to the isoxazolo[5,4-e]indazole (XVII).The aldoxime (XIII) is easily dehydrated to 3-methyl-l-(2-pyridyl)-4-chloro-5-cyano-6,7-dihydroindazole (XVIII) by boiling in acetic anhydride. Nucleophilic substitution of the chlorine atom in the latter is realized by the action of sodium alkoxide and also of potassium hydroxide and leads to the formation of the 4-ethoxy derivative (XIX) and 3-methyl-4-oxo-l-(2-pyridyl)-5-cyano-4,5,6,7-tetrahydroindazole (XX) respectively. The strong absorption band of the carbonyl group in the latter is found at 1686 cm -l, while vc__-N is formed at 2250 cm -1. The cyano ketone (XX) was also obtained by the action of hydroxylamine on 4-acetoxy-5-formylindazole (XV) in pyridine.

show abstract

“…3-Methyl-l-phenyl-5-formyl-4-chloro-6,7-dihydroindazole (III) also reacts with 3-and 4-pyridinecarbamidines [2].…”

mentioning

confidence: 98%

Reactions of 3-methyl-1-(2-pyridyl)-4-chloro-5-formyl-6,7-dihydroindazole

Strakova¹,

Delyatitskaya²,

Петрова³

et al. 1998

Chem Heterocycl Compd

Self Cite

View full text Add to dashboard Cite

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

hi@scite.ai

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

ChemInform Abstract: Synthesis of Heterocyclic Compounds from Cyclohexane‐1,3‐diones

Cited by 1 publication

References 0 publications

Reactions of 3-methyl-1-(2-pyridyl)-4-chloro-5-formyl-6,7-dihydroindazole

Reactions of 3-methyl-1-(2-pyridyl)-4-chloro-5-formyl-6,7-dihydroindazole

Contact Info

Product

Resources

About