tailieunhanh - Synthesis of 4-hydroxy-1-methyl-4-(2-furyl)-3-(2- furylhydroxymethyl) piperidine and Transformation into perhydro [1,3,2] dioxaborinino [5,4-c] pyridine

Having been synthesized successfully heterocyclic system, namely 2-aryl-N-methyl- 4,8a-di(2-furyl)perhydro[1,3,2]dioxaborinino-[5,4-c]pyridine contains two piperidine and dioxaborinine rings. This new heterocyclic system was prepared from the reaction of 4-hydroxy-1- methyl-4-(2-furyl)-3-(2-furylhydroxymethyl)piperidine and some derivatives of arylboronic acid. | VNU Journal of Science: Natural Sciences and Technology, Vol. 33, No. 3 (2017) 98-104 Synthesis of 4-hydroxy-1-methyl-4-(2-furyl)-3-(2furylhydroxymethyl)piperidine and Transformation into perhydro[1,3,2]dioxaborinino[5,4-c]pyridine Nguyen Thi Thanh Phuong1, Tran Thi Thanh Van1,*, Le Tuan Anh1, Truong Hong Hieu2, Tran Thach Van1, Dao Thi Nhung1, Kolyadina , Soldatenkov 1 Faculty of Chemistry, VNU University of Science, 19 Le Thanh Tong, Hanoi, Vietnam Department of Biotechnology, Vietnam-Russia Tropical Centre, 58 Nguyen Van Huyen, Hanoi, Vietnam 3 Department of Chemistry, Peoples’ Friendship University of Russia, 117198 Moscow, Russia 2 Received 08 May 2017 Revised 08 June 2017; Accepted 12 September 2017 Abstract: Having been synthesized successfully heterocyclic system, namely 2-aryl-N-methyl4,8a-di(2-furyl)perhydro[1,3,2]dioxaborinino-[5,4-c]pyridine contains two piperidine and dioxaborinine rings. This new heterocyclic system was prepared from the reaction of 4-hydroxy-1methyl-4-(2-furyl)-3-(2-furylhydroxymethyl)piperidine and some derivatives of arylboronic acid. The structure of new substances was confirmed by physical-chemical method including 1Н NMR, IR, MS. Futhermore, PASS online program investigated that di(2-furyl) perhydro[1,3,2]dioxaborinino[5,4-c]pyridine derivatives have high potential of bioactivities such as dermatology, spasmology, anticoagulant and antipsoriatic agent which promote us to develop the new method affording this kind of compounds. Keywords: piperidine, dioxaborinine, Mannich reaction, multicomponent condensation reaction, azacrown ether. 1. Introduction substituent at 4-position show diversely bioactivities and have great attraction of scienctists around the world [3,4]. By basing on here mentioned facts and as a part of our ongoing research effort focusing on transfer (3) to azacrown ethers [5] and also synthesis of novel dioxaborinine [6,7,8], we have successfully prepared perhydrodioxaborinine (5 .