Lewis acid-promoted cascade reaction of primary amine, 2-butynedioate, and propargylic alcohol: a convenient approach to 1,2-dihydropyridines and 1H-pyrrolo[3,4-b]pyridine-5,7(2H,6H)-diones

1,2-Dihydropyridine-5,6-dicarboxylates were efficiently constructed through a cascade reaction of primary amine, 2-butynedioate and propargylic alcohol in the presence of Lewis acid under mild conditions. As exceptional, 1H-pyrrolo[3,4-b]pyridine-5,7(2H,6H)-diones were approached when the primary am...

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Bibliographic Details
Published inTetrahedron Vol. 69; no. 39; pp. 8353 - 8359
Main Authors Yin, Guangwei, Zhu, Yuanxun, Wang, Ningning, Lu, Ping, Wang, Yanguang
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 30.09.2013
Elsevier
Subjects
Alcohols
Amines
Cascade chemical reactions
Cascade reactions
Chemistry
Chemistry, Organic
Construction
Dihydropyridines
Formations
Heterocycles
Lewis acid
Physical Sciences
Propargylic alcohols
Science & Technology
Tetrahedrons
Trapping
Lewis acid
Heterocycles
DBDBLBHPIVAXPD-UHFFFAOYSA-N
Dihydropyridines
Propargylic alcohols
Cascade reactions
SQAIOEJZQJSKBW-UHFFFAOYSA-N
ASYMMETRIC-SYNTHESIS
ANALOGS
CHEMISTRY
STEREOSELECTIVE-SYNTHESIS
ALKALOIDS
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Summary:1,2-Dihydropyridine-5,6-dicarboxylates were efficiently constructed through a cascade reaction of primary amine, 2-butynedioate and propargylic alcohol in the presence of Lewis acid under mild conditions. As exceptional, 1H-pyrrolo[3,4-b]pyridine-5,7(2H,6H)-diones were approached when the primary amine was methylamine. Possible mechanism for the formation of 1,2-dihydropyridine skeleton is proposed. The process involves 1,3,4-pentatrien-1-amine as a key intermediate that formed in situ by trapping allenic carbocations with enamines. [Display omitted]
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2013.07.076