Chemistry of Heterocyclic Compounds.
Латвийский институт органического синтеза Латвийской академии наук / Springer New York Consultants Bureau.
Vol. 40.
2004.
P. 490-495
Intramolecular Diels - Alder reaction of 4-(N-furfuryl)aminobut-1-enes. New approach to the synthesis of 6,8a-epoxyoctahydroisoquinoline (3-aza-11-oxatricyclo[6.2.1.0 1,6]undec-9-ene) derivatives
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[6.2.1.0 1,6]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.
Authors
Zubkov F.I.
1
,
Nikitina E.V.
1
,
Turchin K.F.2
,
Safronova A.A.
1
,
Borisov R.S.
1
,
Varlamov A.V.
1
Journal
Number of issue
4
Language
English
Pages
860-872
Status
Published
Link
Volume
53
Year
2004
Organizations
- 1 Peoples Friendship Univ. of Russia, 6 Ul. Miklukho-Maklaya, 117198 Moscow, Russian Federation, Russian Federation
- 2 Center for Drug Chemistry, All-Russ. Chem. Pharmaceutical R., 7 Zubovskaya Ul., 119815 Moscow, R., Russian Federation
Keywords
3-aza-11-oxatricyclo[6. 2.1.0 1,6]undec-9-enes; 6,8a-epoxyoctahydroisoquinolines; furans; homoallylamines; intramolecular [4+2]-cycloaddition; intramolecular Diels - Alder reaction
Date of creation
19.10.2018
Date of change
13.08.2021
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Other records
Computational Mathematics and Mathematical Physics.
Vol. 44.
2004.
P. 552-574