4a,7a-Dihydroxy-1-(2-hydroxyethyl)-5-methyl-2′,3′,4a,5′,6′,7a-hexahydrospiro[cyclopenta[b]pyridine-4,4′-pyran]-2,7(1H,3H)-dione

被引：0

作者：

Komogortsev, Andrey N. ^{[1
]}

Lichitsky, Boris V. ^{[1
]}

Melekhina, Valeriya G. ^{[1
]}

机构：

[1] Russian Acad Sci, N D Zelinsky Inst Organ Chem, Leninsky Pr 47, Moscow 119991, Russia

来源：

MOLBANK | 2022年 / 2022卷 / 04期

关键词：

allomaltol; ESIPT-process; photochemical transformations; green chemistry; PROTON-TRANSFER ESIPT; PHOTOCHEMICAL-REACTIONS; TERARYLENES;

D O I：

10.3390/M1481

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An environment-friendly photochemical approach to the synthesis of 4a,7a-dihydroxy-1-(2-hydroxyethyl)-5-methyl-2 ',3 ',4a,5 ',6 ',7a-hexahydrospiro[cyclopenta[b]pyridine-4,4 '-pyran]-2,7(1H,3H)-dione from 2-(4-(3-hydroxy-6-methyl-4-oxo-4H-pyran-2-yl)tetrahydro-2H-pyran-4-yl)-N-(2-hydroxyethyl)acetamide was elaborated. The suggested method is based on the ESIPT-promoted contraction of 3-hydroxypyran-4-one fragment followed by intramolecular cyclization of generated in situ alpha-hydroxy-1,2-diketone intermediate. The distinctive feature of the presented protocol is the employment of water as a solvent for the considered photoreaction. The structure of the obtained photoproduct was confirmed by H-1, C-13-NMR, IR spectroscopy and high-resolution mass spectrometry.

引用

页数：4

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