том 68 издание 2 страницы 403-414

Synthesis of 1,2-Dihydropyridines, 2,3-Dihydro-4(1H)-pyridinone, and 1,2,3,4-Tetrahydropyridinesvia N-AcylN,O-Hemiacetal Formation

Тип публикацииJournal Article
Дата публикации1985-03-27
scimago Q2
wos Q3
БС2
SJR0.491
CiteScore3.0
Impact factor1.8
ISSN0018019X, 15222675
Catalysis
Organic Chemistry
Drug Discovery
Biochemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Краткое описание
New procedures are described for the synthesis of α,β-ethylenic and acetylenic aldehydes from 2-butene- and 2-butyne-1,4-diol, respectively (see Scheme 1). These are applied to the preparation of a particular δ-acetylamino-α,β-ethylenic aldehyde ((E)-5) as well as of its acetylenic analogue 15. On heating in the presence of a silyl enol ether, the former undergoes a complete dehydrative cyclization affording the N-acetyl-1,2-dihydropyridine 19. The addition of HCl to aldehyde (E)-5 results in the production of the 4-chloro-1,2,3,4-tetrahydropyridine 22 which is hydrolyzed to the corresponding alcohol 23 on silica gel. Similarly, the addition of HCl or HBr to the δ-acetyl-amino-α,β-acetylenic aldehyde 15 leads to the previously unknown 4-halo-1,2-dihydropyridines 26; these are easily hydrolyzed to the 2,3-dihydro-4(1H)-pyridinone 27. The ring-forming process involves a N-acyl N,O-hemiacetal as intermediate which is eventually dehydrated.
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ГОСТ |
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Roduit J. P., Wyler H. Synthesis of 1,2-Dihydropyridines, 2,3-Dihydro-4(1H)-pyridinone, and 1,2,3,4-Tetrahydropyridinesvia N-AcylN,O-Hemiacetal Formation // Helvetica Chimica Acta. 1985. Vol. 68. No. 2. pp. 403-414.
ГОСТ со всеми авторами (до 50) Скопировать
Roduit J. P., Wyler H. Synthesis of 1,2-Dihydropyridines, 2,3-Dihydro-4(1H)-pyridinone, and 1,2,3,4-Tetrahydropyridinesvia N-AcylN,O-Hemiacetal Formation // Helvetica Chimica Acta. 1985. Vol. 68. No. 2. pp. 403-414.
RIS |
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TY - JOUR
DO - 10.1002/hlca.19850680214
UR - https://doi.org/10.1002/hlca.19850680214
TI - Synthesis of 1,2-Dihydropyridines, 2,3-Dihydro-4(1H)-pyridinone, and 1,2,3,4-Tetrahydropyridinesvia N-AcylN,O-Hemiacetal Formation
T2 - Helvetica Chimica Acta
AU - Roduit, Jean Paul
AU - Wyler, Hugo
PY - 1985
DA - 1985/03/27
PB - Wiley
SP - 403-414
IS - 2
VL - 68
SN - 0018-019X
SN - 1522-2675
ER -
BibTex |
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@article{1985_Roduit,
author = {Jean Paul Roduit and Hugo Wyler},
title = {Synthesis of 1,2-Dihydropyridines, 2,3-Dihydro-4(1H)-pyridinone, and 1,2,3,4-Tetrahydropyridinesvia N-AcylN,O-Hemiacetal Formation},
journal = {Helvetica Chimica Acta},
year = {1985},
volume = {68},
publisher = {Wiley},
month = {mar},
url = {https://doi.org/10.1002/hlca.19850680214},
number = {2},
pages = {403--414},
doi = {10.1002/hlca.19850680214}
}
MLA
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Roduit, Jean Paul, and Hugo Wyler. “Synthesis of 1,2-Dihydropyridines, 2,3-Dihydro-4(1H)-pyridinone, and 1,2,3,4-Tetrahydropyridinesvia N-AcylN,O-Hemiacetal Formation.” Helvetica Chimica Acta, vol. 68, no. 2, Mar. 1985, pp. 403-414. https://doi.org/10.1002/hlca.19850680214.