Proceedings 2019, 9, 1; doi:10.3390/ecsoc-22-05794 www.mdpi.com/journal/proceedings Extended Abstract A New Approach to the Synthesis of Functionalized Bicyclo[3.2.1]octanes † Arif Idris Ismiev 1 , Gunay Zakhid Mamedova 1 , Victor V. Dotsenko 2,3,4, *, Nikolai A. Aksenov 3 , Inna V. Aksenova 3 and Abel Mamedali Magerramov 1 1 Department of Chemistry, Baku State University, Akademik Zahid Xəlilov küçəsi-23, Baku 1148, Azerbaijan; arif_ismiev@mail.ru (A.I.I.); gunka479@mail.ru (G.Z.M.); rector@bsu.az (A.M.M.) 2 Department of Chemistry and High Technologies, Kuban State University, 149 Stavropolskaya Str., 350040 Krasnodar, Russia 3 Department of Chemistry, North Caucasus Federal University, 1a Pushkina Str., 355009 Stavropol, Russia; radioanimation@rambler.ru (N.A.A.); inna-aksenova00@rambler.ru (I.V.A.) 4 ChemEx Lab, Vladimir Dal’ Lugansk National University, 20A Molodezhny, 91034 Lugansk, Russia * Correspondence: victor_dotsenko_@mail.ru † Presented at the 22nd International Electronic Conference on Synthetic Organic Chemistry, 15 November–15 December 2018; Available Online: https://sciforum.net/conference/ecsoc-22. Published: 14 November 2018 Abstract: The reaction of furfural with secondary amines and isopropyl cyanoacetate leads to the formation of the previously unknown diisopropyl 8-(dialkylamino)-2,4-dicyano-3-(2-furyl)-6- oxobicyclo[3.2.1]octane-2,4-dicarboxylates. The structures of the products were confirmed by NMR and X-ray analysis. Keywords: furfural; isopropyl cyanoacetate; Stenhouse salt; Nazarov reaction; carbocyclization; bicyclo[3.2.1]octane Recently, a number of papers [1–6] dealing with the development of various approaches to the synthesis of bicyclo[3.2.1]octanes have appeared (for reviews, see [7–9]). First, this bicyclic system is of interest due to its biological activity—inhibitors of dopamine and serotonin transfer [10] were found among bicyclo[3.2.1]octanes. They can also be used in the synthesis of tricyclic terpenoids [11]. The bicyclo[3.2.1]octane motif is the structural core unit of various natural terpene compounds and alkaloids [8]. In continuation of our studies in the chemistry of active methylene nitriles [12–16], we would like to propose a new approach to the synthesis of bicyclo[3.2.1]octanes based on an elegant cascade reaction between furfural and isopropyl cyanoacetate in the presence of secondary amines. We found that the reaction of furfural with secondary amines and cyanoacetic ester leads to the formation of bicyclooctanes 1a,b (Scheme 1)in moderate yields (37%–45%). Scheme 1. Synthesis of compounds 1.