ALKYL NITRATE NITRATION OF ACTIVE METHYLENE-COMPOUNDS .15. NITRATION OF 1-METHYL-4-PIPERIDONE, 1-METHYL-2-PYRROLIDINONE AND 1,3-DIMETHYL-2-PYRROLIDINONE

被引：4

作者：

FEUER, H

BLECKER, LR

JANS, RW

FROST, JW

机构：

[1] Department of Chemistry, Purdue University, West Lafayette, Indiana

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 1979年 / 16卷 / 03期

关键词：

D O I：

10.1002/jhet.5570160314

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of 1‐methyl‐4‐piperidone (1) with amyl nitrate in the potassium tert‐butoxidetetrahydrofuran system gave dipotassium 5‐methyl‐2‐oxo‐1,3‐piperidinedinitronate (4) in 78% yield. Similar treatment of 1‐methyl‐2‐pyrrolidinone (2) afforded potassium 3‐methyl‐2‐oxopyrrolidinenitronate (7) in 85% yield. In contrast, the nitration of 1,3‐dimethyl‐2‐pyrrolidinone (3) led to opening of the lactam ring with the formation of amyl 2‐aza‐2‐methyl‐5‐nitrohexanoate (10) in 40% yield. Acidification of disalt 4 did not cause ring opening but gave the dipolar ion of 1‐methyl‐3‐nitro 4‐hydroxy‐5‐aci‐nitro‐Δ3‐tetrahydropyridinium (6). Copyright © 1979 Journal of Heterocyclic Chemistry

引用

页码：481 / 485

页数：5

共 14 条

[1]

ADAMS R, 1941, J AM CHEM SOC, V63, P225

[2]

BELLAMY LJ, 1954, INFRARED SPECTRA COM, P90

[3]

BROWN HC, 1962, HYDROBORATION, P249

[4] ALKYL NITRATE NITRATION OF ACTIVE METHYLENE-COMPOUNDS .13. NITRATION OF ALDIMINES [J].