New syntheses of [1,2,5]oxadiazolo[3,4-e][1,2,3,4]tetrazine 4,6-dioxide

被引：30

作者：

Zelenov, V. P. ^{[1
]}

Lobanova, A. A. ^{[2
]}

Sysolyatin, S. V. ^{[3
]}

Sevodina, N. V. ^{[2
]}

机构：

[1] Russian Acad Sci, Zelinskii Inst Organ Chem, Moscow 119991, Russia

[2] Altay Fed Res & Prod Ctr, Biisk, Altay Krai, Russia

[3] Russian Acad Sci, Siberian Branch, Inst Problems Chem & Energet Technol, Biisk, Altay Krai, Russia

来源：

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 49卷 / 03期

关键词：

DIAZENE N-OXIDES; HALO COMPOUNDS; CHEMISTRY; NITRATION; ENTHALPY; AMINES; ACID;

D O I：

10.1134/S107042801303024X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New methods were developed for the synthesis of [1,2,5]oxadiazolo[3,4-e][1,2,3,4]tetrazine 4,6-dioxide from 4-(tert-butyl-NNO-azoxy)-N-nitro-1,2,5-oxadiazol-3-amine or its alkali metal salts and acid anhydrides (or chlorides) in the presence of strong acids. The yield of [1,2,5]oxadiazolo[3,4-e][1,2,3,4]tetrazine 4,6-dioxide in acetic anhydride in the presence of sulfuric acid or sulfuric anhydride at 20A degrees C in 20 min attained 83%. A general mechanism was proposed for the reactions under study. Acetyl group behaved for the first time as departing group in the synthesis 1,2,3,4-tetrazine 1,3-dioxides, and [1,2,5]oxadiazolo[3,4-e][1,2,3,4]tetrazine 4,6-dioxide was obtained in 47% yield from N-[4-(acetyl-NNO-azoxy)-1,2,5-oxadiazol-3-yl]acetamide.

引用

页码：455 / 465

页数：11

共 50 条

[1] New syntheses of [1,2,5]oxadiazolo[3,4-e][1,2,3,4]tetrazine 4,6-dioxide
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