Catalytic Hydrogenation of 5,6‐Dihydro‐4H‐1,2‐oxazines Bearing a Functionalized Methylene Group at C‐3

Catalytic Hydrogenation of 5,6‐Dihydro‐4H‐1,2‐oxazines Bearing a Functionalized Methylene Group at C‐3 Full article

Journal

European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690

Output data

Year: 2008, Volume: 2008, Number: 23, Pages: 4025-4034 Pages count : 10 DOI: 10.1002/ejoc.200800288

Authors

Sukhorukov Alexey Yu. ¹ , Lesiv Alexey V. ¹ , Eliseev Oleg L. ¹ , Khomutova Yulia A. ¹ , Ioffe Sema L. ¹ , Borissova Alexandra O. ²

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp. 47, 119991 Moscow, Russian Federation,
2	A. N. Nesmeyanov Institute of Organoelement Compounds, Vavilov Str. 28, 119991 Moscow, Russian Federation

The catalytic hydrogenation of readily available methyl 2-(5,6-dihydro-4H-1,2-oxazin-3-yl)acetates 6 has been studied. Dihydrooxazines 6 without an alkoxy substituent at C-6 under mild hydrogenation conditions in methanol produce a dynamic mixture of enamines 7 and tetrahydro-2-furanamines 7′(α + β). These products can be transformed into 1,4-amino alcohols 8 under more robust hydrogenation conditions or into isomeric dihydrofurans 9 and 10 if the reduction is carried out in glacial acetic acid. Reduction of dihydrooxazines 6h,i, which possess an alkoxy substituent at C-6, under similar conditions affords pyrrolidine derivatives 12, 13 and 14. A general mechanistic scheme for the hydrogenation reaction that involves an initial N–O bond cleavage has been suggested.

Sukhorukov A.Y. , Lesiv A.V. , Eliseev O.L. , Khomutova Y.A. , Ioffe S.L. , Borissova A.O.
Catalytic Hydrogenation of 5,6‐Dihydro‐4H‐1,2‐oxazines Bearing a Functionalized Methylene Group at C‐3
European Journal of Organic Chemistry. 2008. V.2008. N23. P.4025-4034. DOI: 10.1002/ejoc.200800288 WOS Scopus OpenAlex

Web of science:	WOS:000258809100016
Scopus:	2-s2.0-53849133470
OpenAlex:	W2083445991

DB	Citing
OpenAlex	16
Scopus	18
Web of science	18