Synthesis of Tetrahydropyrazolo[1,5-c]pyrimidine-2,7(1H,3H)-diones

被引：5

作者：

Groselj, Uros ^{[1
]}

Podlogar, Anja ^{[1
]}

Novak, Ana ^{[1
]}

Dahmann, Georg ^{[2
]}

Golobic, Amalija ^{[1
]}

Stanovnik, Branko ^{[1
]}

Svete, Jurij ^{[1
]}

机构：

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

[2] Boehringer Ingelheim Pharma GmbH & Co KG, Med Chem, D-88397 Biberach, Germany

来源：

SYNTHESIS-STUTTGART | 2013年 / 45卷 / 05期

关键词：

pyrazolo[1,5-c]pyrimidines; cyclization; saturated heterocycles; 3-pyrazolidinones; DERIVATIVES;

D O I：

10.1055/s-0032-1318107

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of tetrahydropyrazolo[1,5-c]pyrimidine2,7(1H,3H)-diones 3a-h as the first representatives of the so far unexplored saturated heterocyclic system have been synthesized, formally in 12 steps from methyl acrylate (4). The synthesis comprises a four-step preparation of methyl N-Cbz-5-alkylamino-3-oxopentanoates 9a-c, their three-step transformation into 5-{2-[(alkyl)(benzyloxycarbonyl)amino]ethyl}pyrazolidin-3-ones 12a-c, three-step selective alkylation of the amidic N-2 to give 2-alkyl-5{2-[(alkyl)(benzyloxycarbonyl) amino] ethyl} pyrazolidin-3-ones 16b-h, followed by hydrogenolytic Cbz-deprotection and subsequent cyclization of the intermediate 1,4-diamine with CDI to furnish the title compounds 3. Most of the synthetic steps were performed as a one-pot transformation.

引用

页码：639 / 650

页数：12

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