1,2,3‐Tricarbonylverbindungen, XII. Konstitutionsermittlung der Reaktionsprodukte von Ninhydrin mit 2‐Aminophenol bzw. 2‐Aminothiophenol

Schönberg, Alexander; Singer, Erich; Hoyer, G.‐A.; Rosenberg, Douwe

doi:10.1002/cber.19771101229

Cited by 13 publications

(9 citation statements)

References 7 publications

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“…Similar reactions in solution were reported to provide only 60 % yield. [7] Compound 10 is remarkably stable: It does not form a spiro-N/S-acetal upon heating up to its melting point at 227 8C.…”

Section: Resultsmentioning

confidence: 99%

“…Figure 5 shows the results on (1)(2)(3)(4)(5)(6)(7)(8)(9)(10). Irrespective of the roughness in Figure 5 a, isolated island hills formed at the remarkably large distance of 0.5 mm by long-range molecular movements.…”

Section: Aminal Structuresmentioning

confidence: 96%

“…The crystal packing in Figure 6 clearly indicates that the functional groups are available for reaction on the (1)(2)(3)(4)(5)(6)(7)(8)(9)(10) surface. The product molecule 8 a can exit along the steep cleavage plane (100) and thus build the island mountains around nucleation sites while reacting molecules of 7 a enter the lattice.…”

Section: Aminal Structuresmentioning

confidence: 99%

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Quantitative Reaction Cascades of Ninhydrin in the Solid State

2002

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Section: Resultsmentioning

confidence: 99%

Section: Aminal Structuresmentioning

confidence: 96%

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Quantitative Reaction Cascades of Ninhydrin in the Solid State

2002

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“…The only literature reference to compound 1 [1] describes the preparation by the reaction of ninhydrin and furazan-3,4-diamine [2] under acidic conditions. This reaction is analogous to that of ninhydrin with o-phenylenediamine and other heterocyclic diamines [3][4][5]. We were interested in preparing derivatives of 1 for biological testing by introducing functionality at positions 6-8 of the tetracycle.…”

mentioning

confidence: 97%

Preparation of 6‐, 7‐, and 8‐substituted derivatives of 2‐Oxa‐1,3,4,10‐tetraazacyclopenta[b]fluoren‐9‐one

Bratton

Unangst

Rubin

et al. 2001

Journal of Heterocyclic Chem

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The preparation of a variety of derivatives of 2-oxa-1,3,4,10-tetraazacyclopenta [b]fluoren-9-one 1 is described. A series of substituted indan-1-ones were prepared and oxidized with N-bromosuccinimide and dimethyl sulfoxide to the corresponding ninhydrin derivatives. Cyclization of the ninhydrins with furazan-3,4-diamine yielded the target tetracycles. Appropiate choice of substituents in ninhydrins led to a preference for one regioisomer in the target tetracycles. This permitted the synthesis of a variety of 8-substituted heterocycles. In those instances where isomer formation was possible, structural assignments were confirmed by X-ray crystallography.J. Heterocyclic Chem., 38, 1103 (2001).As a part of a screening program to identify new compounds with pharmacological activity, we became interested in 2-oxa-1,3,4,10-tetraazacyclopenta[b]fluoren-9-one 1. The only literature reference to compound 1 [1] describes the preparation by the reaction of ninhydrin and furazan-3,4-diamine [2] under acidic conditions. This reaction is analogous to that of ninhydrin with o-phenylenediamine and other heterocyclic diamines [3][4][5]. We were interested in preparing derivatives of 1 for biological testing by introducing functionality at positions 6-8 of the tetracycle. We found that electrophilic aromatic substitution to 1 (bromination, nitration, or Friedel-Crafts acylation with benzoyl chloride) was unsatisfactory, presumably due to deactivation of the aromatic ring by the ketone and fused pyrazine moieties. Ultimately, our method of choice to synthesize these derivatives was to incorporate a suitable functional group into an indan-1-one for conversion to a substituted ninhydrin derivative [6,7] before cyclization with furazan-3,4-diamine.

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“…[424][425] Scheme 123. The condensation of ortho-aminophenols and N-benzylsulfonyl-o-phenylenediamine with ninhydrin.…”

mentioning

confidence: 99%

Ninhydrin in synthesis of heterocyclic compounds

Ziarani¹,

Lashgari²,

Azimian³

et al. 2015

Arkivoc

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Ninhydrin has been utilized in many heterocyclic preparations and considered as an important building block in organic synthesis. There is a wide range of reactions that include ninhydrin in the synthesis of heterocyclic compounds. This review highlights the advances in the use of ninhydrin as starting material in the synthesis of various organic compounds and drugs in a fully comprehensive way, from its first isolation in 1910 to the end of 2013. There is also a diversity of multi-component reactions of ninhydrin and we highlight the recent reports in this review.

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1,2,3‐Tricarbonylverbindungen, XII. Konstitutionsermittlung der Reaktionsprodukte von Ninhydrin mit 2‐Aminophenol bzw. 2‐Aminothiophenol

Cited by 13 publications

References 7 publications

Quantitative Reaction Cascades of Ninhydrin in the Solid State

Quantitative Reaction Cascades of Ninhydrin in the Solid State

Preparation of 6‐, 7‐, and 8‐substituted derivatives of 2‐Oxa‐1,3,4,10‐tetraazacyclopenta[b]fluoren‐9‐one

Ninhydrin in synthesis of heterocyclic compounds

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