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 |
|
||||
| Affiliations |
|
Abstract:
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
Cite:
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 OpenAlex
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 OpenAlex
Dates:
| Published print: | Sep 30, 1994 |
Identifiers:
| Scopus: | 2-s2.0-84988110422 |
| OpenAlex: | W2952968359 |