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Synthesis of a new series of biologically interesting 6'-chloro-1',1'-dioxospiro[4H-benzo[d][1,3,7]oxadiazocine-4,3'(2'H)-[1,4,2]benzodithiazine]-2,6(1H,5H)dione derivatives.

Brzozowski Z, Żołnowska B, Sławiński J - Monatsh. Chem. (2013)

Bottom Line: A series of 6'-chloro-1',1'-dioxospiro[4H-benzo[d][1,3,7]oxadiazocine-4,3'(2'H)-[1,4,2]benzodithiazine]-2,6(1H,5H)dione derivatives have been synthesized from isatoic anhydride and 3-(R(2)-amino)-1,4,2-benzodithiazine 1,1-dioxides.Some synthetic limitations are discussed on the basis of quantum chemical calculations performed by use of the Hartree-Fock method.

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Affiliation: Department of Organic Chemistry, Medical University of Gdańsk, Gen. J. Hallera Str. 107, 80416 Gdańsk, Poland.

ABSTRACT

Abstract: A series of 6'-chloro-1',1'-dioxospiro[4H-benzo[d][1,3,7]oxadiazocine-4,3'(2'H)-[1,4,2]benzodithiazine]-2,6(1H,5H)dione derivatives have been synthesized from isatoic anhydride and 3-(R(2)-amino)-1,4,2-benzodithiazine 1,1-dioxides. Some synthetic limitations are discussed on the basis of quantum chemical calculations performed by use of the Hartree-Fock method.

No MeSH data available.


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Mentions: As shown in Scheme 2, synthesis of the target 6′-chloro-1′,1′-dioxospiro[4H-benzo[d][1,3,7]oxadiazocine-4,3′(2′H)-[1,4,2]benzodithiazine]-2,6(1H,5H)dione derivatives 2–17 was achieved in good to excellent yield (81–97 %) by a convenient procedure starting from isatoic anhydride and benzodithiazines 1a–1p. However, reaction with benzodithiazines 1r, 1s, and 1t failed. In these instances the substrates, only, were recovered from the resulting reaction mixture, i.e. isatoic anhydride (85–89 %) and the corresponding 3-aminobenzodithiazines 1r (69 %), 1 s (59 %), or 1t (69 %).


Synthesis of a new series of biologically interesting 6'-chloro-1',1'-dioxospiro[4H-benzo[d][1,3,7]oxadiazocine-4,3'(2'H)-[1,4,2]benzodithiazine]-2,6(1H,5H)dione derivatives.

Brzozowski Z, Żołnowska B, Sławiński J - Monatsh. Chem. (2013)

·
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4495064&req=5

Sch2: ·
Mentions: As shown in Scheme 2, synthesis of the target 6′-chloro-1′,1′-dioxospiro[4H-benzo[d][1,3,7]oxadiazocine-4,3′(2′H)-[1,4,2]benzodithiazine]-2,6(1H,5H)dione derivatives 2–17 was achieved in good to excellent yield (81–97 %) by a convenient procedure starting from isatoic anhydride and benzodithiazines 1a–1p. However, reaction with benzodithiazines 1r, 1s, and 1t failed. In these instances the substrates, only, were recovered from the resulting reaction mixture, i.e. isatoic anhydride (85–89 %) and the corresponding 3-aminobenzodithiazines 1r (69 %), 1 s (59 %), or 1t (69 %).

Bottom Line: A series of 6'-chloro-1',1'-dioxospiro[4H-benzo[d][1,3,7]oxadiazocine-4,3'(2'H)-[1,4,2]benzodithiazine]-2,6(1H,5H)dione derivatives have been synthesized from isatoic anhydride and 3-(R(2)-amino)-1,4,2-benzodithiazine 1,1-dioxides.Some synthetic limitations are discussed on the basis of quantum chemical calculations performed by use of the Hartree-Fock method.

View Article: PubMed Central - PubMed

Affiliation: Department of Organic Chemistry, Medical University of Gdańsk, Gen. J. Hallera Str. 107, 80416 Gdańsk, Poland.

ABSTRACT

Abstract: A series of 6'-chloro-1',1'-dioxospiro[4H-benzo[d][1,3,7]oxadiazocine-4,3'(2'H)-[1,4,2]benzodithiazine]-2,6(1H,5H)dione derivatives have been synthesized from isatoic anhydride and 3-(R(2)-amino)-1,4,2-benzodithiazine 1,1-dioxides. Some synthetic limitations are discussed on the basis of quantum chemical calculations performed by use of the Hartree-Fock method.

No MeSH data available.