Journal of the Chemical Society. Perkin transactions I p. 2553 - 2559 (1996)
Update date:2022-07-29
Topics:
McCullough, Kevin J.
MacTavish, John
Proctor, George R.
Redpath, James
4-Benzyl-4-ethoxycarbonyl-1-substituted piperidines 1 (R1 = PhCH2, PhCO; R2 = PhCH2) cyclise with polyphosphoric acid (PPA) to give spiro[indane-2,4′-piperidin]-1-ones 3 (R = PhCH2, PhCO), while 2-benzyl-2-ethoxycarbonyl-1-methylpiperidine 4 gives the N-methylspiro[indane-2,2′-piperidin]-1-one 5. 3,4,4a,5-Tetrahydrobenz[g]isoquinolin-10(2H)-one 8 arises from PPA treatment of 1-benzoyl-4-benzyl-5-ethoxycarbonyl-1,2,3,4-tetrahydropyridine 7 (R = PhCO) while o-chloranil converts 1-benzoyl-4-benzyl-4-ethoxycarbonyl-1,4-dihydropyridine 6 (R = PhCO) into 4-benzyl-3-ethoxycarbonylpyridine 9. Phenyl(tribromomethyl)mercury reacts with 1-benzoyl-4-benzyl-4-ethoxycarbonyl-1,4-dihydropyridine 2 (R1 = PhCO, R2 = PhCH2) yielding 2-benzoyl-5-benzyl-7,7-dibromo-5-ethoxycarbonyl-2-azabicyclo[4.1.0]hept-3-ene 11, and with 1-benzoyl-4-benzyl-3-ethoxycarbonyl-1,4-dihydropyridine 6 (R = PhCO) to give 2-benzoyl-5-benzyl-7,7-dibromo-4-ethoxycarbonyl-2-azabicyclo[4.1.0]hept-3-ene 12. The structure of the latter is confirmed by X-ray crystallographic analysis. Catalytic hydrogenation of 2-benzoyl-5-benzyl-7,7-dichloro-5-ethoxycarbonyl-2-azabicyclo[4.1.0]hept-3-ene 16 yields 2-benzoyl-5-benzyl-7,7-dichloro-5-ethoxycarbonyl-2-azabicyclo[4.1.0]heptane 21 which cyclises with PPA to give the tetracyclic product 22 in good yield. When 2-benzoyl-5-benzyl-7,7-dichloro-4-ethoxycarbonyl-2-azabicyclo[4.1.0]hept-3-ene 17 is hydrogenated it yields mainly 2-benzoyl-5-benzyl-7,7-dichloro-4-ethoxycarbonyl-2-azabicyclo[4.1.0]heptane 25 but the dibromo analogue 12 under the same conditions gives two components thought to be 2-benzoyl-5-benzyl-7-endo-bromo-4-ethoxycarbonyl-2-azabicyclo[4.1.0]hept-3-ene 24 and 2-benzoyl-5-benzyl-7-exo-bromo-4-ethoxycarbonyl-2-azabicyclo[4.1.0]hept-3-ene 23. Copyright 1996 by the Royal Society of Chemistry.
View MoreSpringchem New Material Technology Co.,Limited
website:http://www.spring-chem.com
Contact:86-21-62885108
Address:602B, Building 1, No. 641, Tianshan Road
Anhui Redstar Pharmaceutical Corp., Ltd
Contact:+86-563-5120837
Address:Jingxian Industrial Development Zone, Anhui , China
PharmaResources(Kaiyuan)CO,.Ltd
Contact:+86-21-50720028
Address:No.3, Beihuan Road, Economic Development District, Kaiyuan City, Tieling City, Liaoning Province, China 112300
Contact:0086-29-88315623
Address:S711, Innovation Bldg No.25 Gaoxin 1st Rd, Xian P.R of China 710075
Hubei Sibo Technology Co.,Ltd.
Contact:0715-6597222
Address:Pan Jia Wan fan Lake Chemical Industrial Park ,Xianning City, Hubei, China
Doi:10.1002/zaac.201300065
(2013)Doi:10.3987/COM-94-S(B)79
(1994)Doi:10.1016/0008-6215(90)84242-M
(1990)Doi:10.1021/jo961794w
(1997)Doi:10.1002/ejoc.200900150
(2009)Doi:10.1021/jm960319n
(1997)
