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Molecules 2012, 17(12), 13879-13890; doi:10.3390/molecules171213879
Article

Novel Rearrangements in the Reactions Directed Toward Preparation of Spiro-N,N-ketals: Reactions of Naphthalene-1,8-diamine with Ninhydrin and Isatin

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Received: 8 October 2012; in revised form: 31 October 2012 / Accepted: 20 November 2012 / Published: 22 November 2012
(This article belongs to the Special Issue Spiro Compounds)
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Abstract: Spiro-N,N-ketal 5, consisting of a phthaloperine heterocyclic ring and a naphtha[1,8-ef][1,4]diazepine ring, was obtained along with spiro-N,N-ketal 2 via 2,2-condensation in the reaction of ninhydrin with naphthalene-1,8-diamine. Their molecular structures were elucidated by X-ray crystal structural analysis. Aside from these spiro compounds, the diazapleiadiene compound 3 formed by 1,2-condensation and the 1,4-isoquinolinedione compound 4 arising from ring expansion were isolated. When isatin was reacted with naphthalene-1,8-diamine, spiro-N,N-ketal 6 and the two 1H-perimidine-based compounds 7 and 8 were isolated. Compound 8 was revealed to undergo a fast dynamic prototropic tautomerization in solution. Plausible mechanisms of the formation of the products are proposed.
Keywords: spiro-N,N-ketals; perimidine; diazapleiadiene; prototropic tautomerism; X-ray structure determination spiro-N,N-ketals; perimidine; diazapleiadiene; prototropic tautomerism; X-ray structure determination
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Akita, M.; Seto, H.; Aoyama, R.; Kimura, J.; Kobayashi, K. Novel Rearrangements in the Reactions Directed Toward Preparation of Spiro-N,N-ketals: Reactions of Naphthalene-1,8-diamine with Ninhydrin and Isatin. Molecules 2012, 17, 13879-13890.

AMA Style

Akita M, Seto H, Aoyama R, Kimura J, Kobayashi K. Novel Rearrangements in the Reactions Directed Toward Preparation of Spiro-N,N-ketals: Reactions of Naphthalene-1,8-diamine with Ninhydrin and Isatin. Molecules. 2012; 17(12):13879-13890.

Chicago/Turabian Style

Akita, Motoko; Seto, Hideyuki; Aoyama, Reiko; Kimura, Junko; Kobayashi, Keiji. 2012. "Novel Rearrangements in the Reactions Directed Toward Preparation of Spiro-N,N-ketals: Reactions of Naphthalene-1,8-diamine with Ninhydrin and Isatin." Molecules 17, no. 12: 13879-13890.


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