PREPARATION OF OPTICALLY PURE 3'-METHYLSPIRO[IMIDAZOLIDINE-4,4'(1'H)-QUINAZOLINE]-2,2',5(3'H)-TRIONE BY COMBINATION OF OPTICAL RESOLUTION AND RACEMIZATION

被引：25

作者：

YAMAGISHI, M

YAMADA, Y

OZAKI, K

DATE, T

OKAMURA, K

SUZUKI, M

MATSUMOTO, K

机构：

[1] TANABE SEIYAKU CO LTD,APPL BIOCHEM RES LAB,16-89 KASHIMA 3 CHOME,OSAKA 532,JAPAN

[2] TANABE SEIYAKU CO LTD,ORGAN CHEM RES LAB,TODA,SAITAMA 335,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 05期

关键词：

D O I：

10.1021/jo00031a043

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Optically pure 3'-methylspiro[imidazolidine-4,4'(1'H)-quinazoline]-2,2',5(3'H)-trione was prepared by optical resolution using brucine as a resolving agent. The resulting optically pure spirohydantoin was racemized by refluxing in 1,2-dichlorobenzene for 17 h, or more effectively upon heating in 10% HCl at 90-degrees-C for 2 h. In the acid-catalyzed racemization, the introduction of difluoromethyl group at the 3-nitrogen of hydantoin ring increased the racemization rate, while the introduction of methyl group at the 3-nitrogen reduced it. These results suggest that the acid-catalyzed racemization proceeds via the N-acyliminium ion generated by the cleavage of the N3-C4 bond of the spirohydantoin ring.

引用

页码：1568 / 1571

页数：4

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