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, Number: 10, Pages: 983-987 Pages count : 5

Tags

NINHYDRIN; HYDROXYLAMINES; INDENO[1,2-B]PYRAZINES

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	N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of Siberian Branch of Russian Academy of Sciences
2	ST PETERSBURG STATE UNIV,PHYS SCI RES INST,ST PETERSBURG 199164,RUSSIA

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 c NaBH4 yields alcohol 10 and the reaction of 6b with NH2OH/AcOH gives a mixture of isomeric oximes (E)-11 and (Z)-11.

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. N10. P.983-987. WOS

Web of science

WOS:A1994PN28800003