Synthesis of bicyclic N,N-enaminals by cyclization of alk-4-ynals with aliphatic diamines in DMSO upon treatment with KOH
Тип публикации: Journal Article
Дата публикации: 2013-11-01
scimago Q3
БС2
SJR: 0.305
CiteScore: 2.8
Impact factor: 1.7
ISSN: 10665285, 15739171
General Chemistry
Краткое описание
A cyclization of alk-4-ynals with aliphatic diamines in DMSO upon treatment with KOH was found to lead to bicyclic N,N-enaminals. The studies of this reaction showed that 1,3-diaminopropane and N-methyl-1,3-diaminopropane gave (E)-6-(arylmethylidene)octahydropyrrolo[1,2-a]pyrimidines in 45—78% yields, whereas 1,2-diaminoethane gave 5-(arylmethylidene)hexahydropyrrolo[1,2-a]imidazoles as mixtures of E- and Z-isomers in up to 75% total yield. The mechanism of these new cascade cyclization reactions includes formation of the equilibrium mixtures of imines and cyclic aminals with subsequent intramolecular hydroamination of the triple bond having considerable ionic character.
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Gvozdev V. D., Shavrin K. N., Nefedov O. M. Synthesis of bicyclic N,N-enaminals by cyclization of alk-4-ynals with aliphatic diamines in DMSO upon treatment with KOH // Russian Chemical Bulletin. 2013. Vol. 62. No. 11. pp. 2430-2437.
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Gvozdev V. D., Shavrin K. N., Nefedov O. M. Synthesis of bicyclic N,N-enaminals by cyclization of alk-4-ynals with aliphatic diamines in DMSO upon treatment with KOH // Russian Chemical Bulletin. 2013. Vol. 62. No. 11. pp. 2430-2437.
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TY - JOUR
DO - 10.1007/s11172-013-0351-3
UR - https://doi.org/10.1007/s11172-013-0351-3
TI - Synthesis of bicyclic N,N-enaminals by cyclization of alk-4-ynals with aliphatic diamines in DMSO upon treatment with KOH
T2 - Russian Chemical Bulletin
AU - Gvozdev, V D
AU - Shavrin, K N
AU - Nefedov, O M
PY - 2013
DA - 2013/11/01
PB - Springer Nature
SP - 2430-2437
IS - 11
VL - 62
SN - 1066-5285
SN - 1573-9171
ER -
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@article{2013_Gvozdev,
author = {V D Gvozdev and K N Shavrin and O M Nefedov},
title = {Synthesis of bicyclic N,N-enaminals by cyclization of alk-4-ynals with aliphatic diamines in DMSO upon treatment with KOH},
journal = {Russian Chemical Bulletin},
year = {2013},
volume = {62},
publisher = {Springer Nature},
month = {nov},
url = {https://doi.org/10.1007/s11172-013-0351-3},
number = {11},
pages = {2430--2437},
doi = {10.1007/s11172-013-0351-3}
}
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Gvozdev, V. D., et al. “Synthesis of bicyclic N,N-enaminals by cyclization of alk-4-ynals with aliphatic diamines in DMSO upon treatment with KOH.” Russian Chemical Bulletin, vol. 62, no. 11, Nov. 2013, pp. 2430-2437. https://doi.org/10.1007/s11172-013-0351-3.