Interaction of 7-oxoоctyl-7-oxooctanoate and bis(7-oxooctyl)hexandioate with phthalic dihydrazide

Ishmuratov, G. Yu.; Yakovleva, M. P.; Shutova, M. A.; Муслухов, Р. Р.; Толстиков, А. Г.

doi:10.6060/mhc140598y

MHC

2014

DOI: 10.6060/mhc140598y

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Interaction of 7-oxoоctyl-7-oxooctanoate and bis(7-oxooctyl)hexandioate with phthalic dihydrazide

G. Yu. Ishmuratov¹,

M. P. Yakovleva²,

M. A. Shutova³

et al.

Abstract: We have studied the interaction of 7-oxoоctyl-7-oxooctanoate and bis(7-oxooctyl)hexanedioate, available from tetrahydropyran, with phthalic dihydrazide. It was found, that instead of expected macrolides containing hydrazide fragments, the corresponding macrocycles containing azine fragments are formed. Such compounds were obtained earlier via the interaction of substrates and hydrazine hydrate.

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2024

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Synthesis of 5,5′-Dinitro- and 5,5′-Diaminobis(cyclopenta[b]indoles) Bound at N4,N4′ Atoms with a Dioxoalkane Spacer

Gataullin,

Складчиков

2024

Žurnal obŝej himii

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Upon condensation of 2 equiv. of 3R*,3aR*,8bS*-3-iodo-7-methyl-1,2,3,3а,4,8b-hexahydrocyclopenta[b]indole with 1 equiv. of glutaric or decanedicarboxylic acid dichloranhydride [N4,N4′-di-(3R*,3aR*,8bS*,3′R*,3a′R*,8b′S*)- and N4,N4′-di-(3aR*,3aR*,8bS*,3′S*,3a′S*,8b′R*)-3-iodo-7-methyl-1,2,3,3а,4,8b-hexahydrocyclopenta[b]indolyl]alkanediamides were synthesized. Their didehydrohalogenation to 3aR*,8bR*,3a′R*,8b′R*- and 3aS*,8bS*,3a′R*,8b′R*-1,3a,4,8b-tetrahydroanalogues was carried out by boiling these diiodides in piperidine. The presence of rotamerism in the products of dehydrohalogenation was shown, which is manifested by doubling the signals in the NMR spectra in different ratios. Nitration with trifluoroacetyl nitrate in CH2Cl2 yielded their 5,5′-dinitro analogs, which, when reacted with freshly prepared Fe(OH)2, along with 5,5′-diamino derivatives, also formed 5-amino-5′-nitro-substituted products of incomplete reduction. When a nitro group or an amino group appears at the C5 and C5′ carbon atoms of the cyclopenta[b]indole fragments, the doubling of the signals in the NMR spectra disappears. The interaction of a 5,5′-diamino derivative (n = 8) with decanedicarboxylic acid dichloride yielded a compound with 30 atoms in the macrocyclic ring.

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Synthesis of 5,5′-Dinitro- and 5,5′-Diaminobis(cyclopenta[b]indoles) Bound at N4,N4′ Atoms with a Dioxoalkane Spacer

Gataullin,

Складчиков

2024

Žurnal obŝej himii

View full text Add to dashboard Cite

show abstract

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Interaction of 7-oxoоctyl-7-oxooctanoate and bis(7-oxooctyl)hexandioate with phthalic dihydrazide

Cited by 1 publication

References 10 publications

Synthesis of 5,5′-Dinitro- and 5,5′-Diaminobis(cyclopenta[<i>b</i>]indoles) Bound at <i>N</i><sup>4</sup>,<i>N</i><sup>4′</sup> Atoms with a Dioxoalkane Spacer

Synthesis of 5,5′-Dinitro- and 5,5′-Diaminobis(cyclopenta[<i>b</i>]indoles) Bound at <i>N</i><sup>4</sup>,<i>N</i><sup>4′</sup> Atoms with a Dioxoalkane Spacer

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