Unusual reactions of 5,5-dimethyl-2-(indenyl-2)-3-pyrazolidinone with acetylenedicarboxylates

被引：13

作者：

Turk, C ^{[1
]}

Svete, J ^{[1
]}

Stanovnik, B ^{[1
]}

Golic, L ^{[1
]}

Golobic, A ^{[1
]}

Selic, L ^{[1
]}

机构：

[1] Univ Ljubljana, Fac Chem & Chem Technol, Ljubljana 1000, Slovenia

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 04期

关键词：

D O I：

10.1021/ol9911829

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Reaction of 5,5-dimethyl-3-pyrazolidinone (1) with 2-indanone (2) gave 5,5-dimethyl-2-(1H-indenyl-2)-3-pyrazolidinone (3) instead of the expected azomethine imine 4. Although reaction of 2 substituted 3-pyrazolidinones with acetylenedicarboxylates usually gives ring expansion products, such as 1,2-diazepines, treatment of 3 with dialkyl acetylenedicarboxylates (5, R = Me; 6 R = Et) resulted in the formation of rel-(7aR,12aS)-6,7-bis (alkoxycarbonyl)-3,4-dihydro-4,4-dimethyl-7aH-indano[1,2-b]pyrrolo[1,2-a]pyrimidin-2-ones (7, R = Me; 9, R = Et) as major products and 3,4-bis(alkoxycarbonyl)-7,7-dimethyl-2-(indenyl-2)-6,7-dihydro-2H,6H-1,2-diazepin-5-ones (8, R = Me: 10, R = Et) as minor products.

引用

页码：423 / 424

页数：2

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