Intramolecular Diels—Alder reaction of 4-(N-furfuryl)aminobut-1-enes. New approach to the synthesis of 6,8a-epoxyoctahydroisoquinoline (3-aza-11-oxatricyclo[6.2.1.01,6]undec-9-ene) derivatives
2
Center for Drug Chemistry, All-Russian Chemical and Pharmaceutical Research Institute, Moscow, Russian Federation
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Publication type: Journal Article
Publication date: 2004-04-01
scimago Q3
SJR: 0.305
CiteScore: 2.8
Impact factor: —
ISSN: 10665285, 15739171
General Chemistry
Abstract
The intramolecular Diels—Alder reaction of readily accessible 4-substituted 4-(N-furfuryl)aminobut-1-enes was studied and a new one-step method was developed for the synthesis of 6,8a-epoxy-1,2,3,4,4a,5,6,8a-octahydroisoquinoline (3-aza-11-oxatricyclo[6.2.1.01,6]undec-9-ene) derivatives. The [4+2]-cycloaddition proceeds stereoselectively to form exo-adducts. The influence of substituents at the nitrogen atom in 4-(N-furfuryl)aminobut-1-enes on the cycloaddition pathway was examined.
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Total citations:
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Citations from 2025:
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Zubkov F. I. et al. Intramolecular Diels—Alder reaction of 4-(N-furfuryl)aminobut-1-enes. New approach to the synthesis of 6,8a-epoxyoctahydroisoquinoline (3-aza-11-oxatricyclo[6.2.1.01,6]undec-9-ene) derivatives // Russian Chemical Bulletin. 2004. Vol. 53. No. 4. pp. 860-872.
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Zubkov F. I., Nikitina E., Turchin K. F., Safronova A., Borisov R. S., Varlamov A. V. Intramolecular Diels—Alder reaction of 4-(N-furfuryl)aminobut-1-enes. New approach to the synthesis of 6,8a-epoxyoctahydroisoquinoline (3-aza-11-oxatricyclo[6.2.1.01,6]undec-9-ene) derivatives // Russian Chemical Bulletin. 2004. Vol. 53. No. 4. pp. 860-872.
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TY - JOUR
DO - 10.1023/B:RUCB.0000037856.61928.c4
UR - https://doi.org/10.1023/B:RUCB.0000037856.61928.c4
TI - Intramolecular Diels—Alder reaction of 4-(N-furfuryl)aminobut-1-enes. New approach to the synthesis of 6,8a-epoxyoctahydroisoquinoline (3-aza-11-oxatricyclo[6.2.1.01,6]undec-9-ene) derivatives
T2 - Russian Chemical Bulletin
AU - Zubkov, F I
AU - Nikitina, E.V
AU - Turchin, K F
AU - Safronova, A.A.
AU - Borisov, R S
AU - Varlamov, A V
PY - 2004
DA - 2004/04/01
PB - Springer Nature
SP - 860-872
IS - 4
VL - 53
SN - 1066-5285
SN - 1573-9171
ER -
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@article{2004_Zubkov,
author = {F I Zubkov and E.V Nikitina and K F Turchin and A.A. Safronova and R S Borisov and A V Varlamov},
title = {Intramolecular Diels—Alder reaction of 4-(N-furfuryl)aminobut-1-enes. New approach to the synthesis of 6,8a-epoxyoctahydroisoquinoline (3-aza-11-oxatricyclo[6.2.1.01,6]undec-9-ene) derivatives},
journal = {Russian Chemical Bulletin},
year = {2004},
volume = {53},
publisher = {Springer Nature},
month = {apr},
url = {https://doi.org/10.1023/B:RUCB.0000037856.61928.c4},
number = {4},
pages = {860--872},
doi = {10.1023/B:RUCB.0000037856.61928.c4}
}
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MLA
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Zubkov, F. I., et al. “Intramolecular Diels—Alder reaction of 4-(N-furfuryl)aminobut-1-enes. New approach to the synthesis of 6,8a-epoxyoctahydroisoquinoline (3-aza-11-oxatricyclo[6.2.1.01,6]undec-9-ene) derivatives.” Russian Chemical Bulletin, vol. 53, no. 4, Apr. 2004, pp. 860-872. https://doi.org/10.1023/B:RUCB.0000037856.61928.c4.