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peri-Naphthalenediamines: XXXIV. 1,4,5,8-Tetrakis(dimethylamino)naphthalene: Alternative Approaches to Synthesis

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Abstract

New methods were proposed for synthesizing 1,4,5,8-tetrakis(dimethylamino)naphthalene with an overall yield of 4 to 12% to replace the known procedure ensuring an overall yield of 2%. Catalytic hydrogenation was shown to be inapplicable for preparation of polyaminonaphthalenes from nitro compounds having 3 or 4 nitro gruops in the α-positions. Nucleophilic amination of 1,5-dinitronaphthalene in the system NH2OH/NaOH/MeOH yields 1-amino-4-nitronaphthalene. The nitration of 1,5-bis(p-tolylsulfonylamino)naphthalene leads to formation of 2,6-dinitro rather than 4,8-dinitro derivative, as it was believed formerly. This was confirmed by transformation of the latter into 1,2,5,6-tetrakis(dimethylamino)naphthalene. 3-Nitro, 2,6-dinitro, 2,6-diamino, and 2,4,6,8-tetranitro derivatives of 1,5-bis(dimethylamino)naphthalene, nitro and amino derivatives of 1,4,5-tris(dimethylamino)naphthalene, and 4,5-diamino-1,8-bis(methylamino)naphthalene were synthesized. By treatment with perchloric acid 1,4,5,8-tetrakis(dimethylamino)naphthalene was oxidized to 2,3-dihydroperimidinium salt.

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Authors and Affiliations

  1. Rostov State University, ul. Zorge 7, Rostov-on-Don, 344090, Russia

    V. I. Sorokin, V. A. Ozeryanskii & A. F. Pozharskii

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  1. V. I. Sorokin
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  2. V. A. Ozeryanskii
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  3. A. F. Pozharskii
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Sorokin, V.I., Ozeryanskii, V.A. & Pozharskii, A.F. peri-Naphthalenediamines: XXXIV. 1,4,5,8-Tetrakis(dimethylamino)naphthalene: Alternative Approaches to Synthesis. Russian Journal of Organic Chemistry 38, 699–708 (2002). https://doi.org/10.1023/A:1019615206870

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