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

共 50 条

[1] The 4a′-Hydroxy-3′,3′,5,6′,6′,7-hexamethyl-3′,4′,4a′,6′,7′,9a′-hexahydrospiro[indole-3,9′-xanthene]-1′,2,8′(1H,2′H,5′H)-trione
Ryzhkova, Yuliya E.
Kalashnikova, Varvara M.
Ryzhkov, Fedor V.
Fakhrutdinov, Artem N.
Elinson, Michail N.
MOLBANK, 2023, 2023 (03)
[2] ACID-CATALYSED REARRANGEMENT OF 4,4A,5,6,7,8-HEXAHYDRO-5-HYDROXY-4A-METHYL-2(3H)-NAPHTHALENONE
LOS, M
MIGHELL, AD
TETRAHEDRON, 1965, 21 (09) : 2297 - &
[3] Enantiomeric 4,4a,7,7a-tetrahydro-1H-cyclopenta[c]pyran-3-ones
Gimazetdinov, Airat M.
Kolesnikova, Tatyana V.
Miftakhov, Mansur S.
MENDELEEV COMMUNICATIONS, 2009, 19 (05) : 275 - 275
[4] 1-[(4aS,5R,7R,7aS)-7-Hydroxymethyl-3,4,4a,5,7,7a-hexahydro-2H-furo[3,4-b][1,4] thiazin-5-yl]pyrimidine-2,4(1H,3H)-dione
Sun, Jing-Bo
Yang, Hua
Wu, Jin-Chang
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2007, 63 : O978 - O979
[5] SOME REACTIONS OF 4A, 5-DIHYDRO-5-PARA-CHLOROPHENYL-7-(2'-METHOXY-1'-NAPHTHYL)-2-METHYL-4(H)-OXOPYRANO[2, 3-B]PYRIDINE AND 4(H)-THIONOPYRANO[2, 3-B]PYRIDINE
ESSAWY, A
ELSAFTY, M
ELGENDY, MA
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1982, 21 (08): : 769 - 772
[6] ISOXAZOLE ANNELATION REACTION - 1-METHYL-4,4A,5,6,7,8-HEXAHYDRONAPHTHALEN-2(3H)-ONE
MCMURRY, JE
ORGANIC SYNTHESES, 1988, 50-9 : 781 - 786
[7] ASYMMETRIC-SYNTHESIS OF 1,4A-DIMETHYL-4,4A,7,8-TETRAHYDRONAPHTHALENE-2(3H),5(6H)-DIONE
COISNE, JM
PECHER, J
DECLERCQ, JP
GERMAIN, G
VANMEERSSCHE, M
BULLETIN DES SOCIETES CHIMIQUES BELGES, 1981, 90 (05): : 481 - 484
[8] Photoinduced assembly of the 3,4,4a,7a-tetrahydro-1H-cyclopenta[b]pyridine-2,7-dione core on the basis of allomaltol derivatives
Milyutin, Constantine, V
Galimova, Renata D.
Komogortsev, Andrey N.
Lichitskii, Boris, V
Melekhina, Valeriya G.
Migulin, Vasily A.
Fakhrutdinov, Artem N.
Minyaev, Mikhail E.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (45) : 9975 - 9985
[9] Ethyl 3-(2,4-dioxocyclohexyl)propanoate as a novel precursor for N-substituted 4,4a,5,6-tetrahydroquinoline-2,7(1H,3H)-diones and their corresponding 3,4-dihydro-7-hydroxyquinolin-2(1H)-ones and 7-hydroxyquinolin-2(1H)-ones synthesis
Thakur, Vandna
Sharma, Dharminder
Das, Pralay
MOLECULAR DIVERSITY, 2016, 20 (01) : 29 - 40
[10] Ethyl 3-(2,4-dioxocyclohexyl)propanoate as a novel precursor for N-substituted 4,4a,5,6-tetrahydroquinoline-2,7(1H,3H)-diones and their corresponding 3,4-dihydro-7-hydroxyquinolin-2(1H)-ones and 7-hydroxyquinolin-2(1H)-ones synthesis
Vandna Thakur
Dharminder Sharma
Pralay Das
Molecular Diversity, 2016, 20 : 29 - 40

← 1 2 3 4 5 →