Synthesis of Indeno[1,2‐b]pyrazine N‐Oxides by Reaction of Ninhydrin with 1,2‐Bishydroxylamines

Synthesis of Indeno[1,2‐b]pyrazine N‐Oxides by Reaction of Ninhydrin with 1,2‐Bishydroxylamines Full article

Journal

Liebigs Annalen der Chemie
ISSN: 0170-2041

Output data

Year: 1994, Volume: 1994, Number: 10, Pages: 983-987 Pages count : 5 DOI: 10.1002/jlac.199419941005

Tags

Hydroxylamines; Indeno[1,2‐b]pyrazines; Ninhydrin

Authors

Mazhukin D.G. ¹ , Tikhonov A.Ya. ¹ , Volodarsky L.B. ¹ , Evlampieva N.P. ² , Vetchinov V.P. ¹ , Mamatyuk V.I. ¹

Affiliations

1	(Scopus) Novosibirsk Institute of Organic Chemistry, Siberian Division of the Russsian Academy of Sciences, Novosibirsk, 630090, Russian Federation
2	(Scopus) Scientific Research Institute of Physics, St. Petersburg State University, St. Petersburg, 199164, Russian Federation

The reaction of the ninhydrin (1) with 1,2‐bishydroxylamines 2a–c affords dihydroindeno[1,2‐b]pyrazine N,N′‐dioxides 5a–c. The intermediates hexahydro‐ and tetrahydroindeno[1,2‐b]pyrazines 3a and 4c, which have been isolated, are easily transformed into 5a, c. Heating of 5b, c or keeping of 5b on alumina gives indeno[1,2‐b]pyrazine N‐oxides 6b, c, N,N′‐dioxide 7c and indeno[1,2‐b]pyrazine 8. Treatment of 5b with a solution of hydrochloric acid in H2O/MeOH leads to 6b, whereas treatment of 5b with KOH furnishes mono‐N‐oxides 6b, 9 and dioxide 7b. Compound 8 is prepared by deoxygenation of 6b with TiCl3. The reduction of 6b with NaBH4 yields alcohol 10 and the reaction of 6b with NH2OH/AcOH gives a mixture of isomeric oximes (E)‐11 and (Z)‐11. Copyright © 1994 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim

Mazhukin D.G. , Tikhonov A.Y. , Volodarsky L.B. , Evlampieva N.P. , Vetchinov V.P. , Mamatyuk V.I.
Synthesis of Indeno[1,2‐b]pyrazine N‐Oxides by Reaction of Ninhydrin with 1,2‐Bishydroxylamines
Liebigs Annalen der Chemie. 1994. V.1994. N10. P.983-987. DOI: 10.1002/jlac.199419941005 Scopus

Published print:

Sep 30, 1994

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