Unexpected Synthesis of 2,3,5,6-Tetrahydro-1H-pyrrolo[3,4-c]pyridine-1,3,6-triones by a Double Michael Addition/CS2 Extrusion/Double Cyclization Sequence

被引：9
作者：
Mari, Giacomo [1 ,2 ]
De Crescentini, Lucia [1 ,2 ]
Favi, Gianfranco [1 ,2 ]
Santeusanio, Stefania [1 ,2 ]
Lillini, Samuele [3 ]
Mantellini, Fabio [1 ,2 ]
机构：
[1] Univ Urbino Carlo Bo, Dept Biomol Sci, Organ Chem Sect, Via I Maggetti 24, I-61029 Urbino, PU, Italy
[2] Univ Urbino Carlo Bo, Organ Nat Cpds, Via I Maggetti 24, I-61029 Urbino, PU, Italy
[3] Dompe Farmaceutici Spa, Via P Castellino, I-80131 Naples, Italy
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 2017卷 / 42期
关键词：
Heterocycles; Hydrazones; Michael addition; Domino reactions; Ring opening; Ring closing; SITU GENERATED 1,2-DIAZA-1,3-DIENES; CATALYTIC ASYMMETRIC-SYNTHESIS; HIV-1 INTEGRASE INHIBITORS; N-SULFONYL HYDRAZONES; DIELS-ALDER REACTION; ORGANIC-SYNTHESIS; CYCLOADDITION REACTIONS; CASCADE REACTIONS; DOMINO REACTIONS; DRUG DISCOVERY;
D O I：
10.1002/ejoc.201701097
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Bis adducts derived from a double Michael addition of rhodanine to an azo-ene system of two molecules of 1,2-diaza-1,3-dienes (DDs) have furnished the corresponding 2,3,5,6-tetrahydro-1H-pyrrolo[3,4-c]pyridine-1,3,6-triones by means of a CS2 extrusion/double cyclization sequence. The incorporation of two units (4 and 2 atoms) of DDs into the fused bicyclic heterocycles represents a new application of this versatile class of molecules in heterocyclic synthesis.
引用
收藏
页码：6291 / 6298
页数：8
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