95687-85-7Relevant articles and documents
Catalyst-Controlled Diastereoselective Synthesis of Cyclic Amines via C-H Functionalization
Munnuri, Sailu,Adebesin, Adeniyi Michael,Paudyal, Mahesh P.,Yousufuddin, Muhammed,Dalipe, Alfonso,Falck, John R.
supporting information, p. 18288 - 18294 (2017/12/27)
Reliable regio- and stereochemical techniques applicable to nonactivated aliphatic systems remain largely elusive due to the challenges of discriminating between multiple, relatively strong sp3 C-H bonds whose chemical behavior often differ onl
Synthesis of bridged azabicyclic compounds using radical translocation reactions of 1-(o-halogenobenzoyl)-2-(prop-2-enyl)-and -(prop-2-ynyl)-piperidines
Ikeda, Masazumi,Kugo, Yasuhiro,Sato, Tatsunori
, p. 1819 - 1824 (2007/10/03)
Methyl 1-(o-bromobenzoyl)-2-(prop-2-enyl)piperidine-2-carboxylate 8a, upon treatment with tributyltin hydride in the presence of azoisobutyronitrile in boiling toluene gave regioselectively the 8-azabicyclo[3.2.1]octane 14a (a 5-exo cyclisation product) in quantitative yield as a diastereomeric mixture (66:34). 1-(o-Bromobenzoyl)-2-(prop-2-enyl)piperidine 13 also gave the 8-azabicyclo-[3.2.1]octane 16 (75% as a diastereomeric mixture), along with the pyrido[2,1-a]isoindolone 17 (10%) and the simple reduction product 18 (5%). 1-(o-Iodobenzoyl)-2-[3-(trimethylsilyl)prop-2-ynyl]piperidine 23 afforded, in addition to the pyrido[2,1-a]isoindolone 25 (18%), the 8-azabicyclo-[3.2.1]octane 24 (75%) which was converted into the 6-oxo derivative 27. For comparison, the behaviour of the azetidine congener 31 was also examined.
Synthesis of bridged azabicyclic compounds using raducal translocation reactions of 1-(o-bromobenzoyl)-2-(prop-2-enyl)pyrrolidines
Sato, Tatsunori,Kugo, Yasuhiro,Nakaumi, Erina,Ishibashi, Hiroyuki,ikeda, Masazumi
, p. 1801 - 1810 (2007/10/02)
A new synthesis of the 7-azabicycloheptane and 8-azabicyclooctane systems is described in which α-acylamino radicals generated from 1-(o-bromobenzoyl-2-(prop-2-enyl)pyrrolidines by a Bu3SnH-mediated radical translocation reaction are cyclised.Treatment of methyl 1-(o-bromobenzoyl)-2-(prop-2-enyl)pyrrolidine-2-carboxylate 3a with Bu3SnH in the presence of a catalytic amount of azoisobutyronitrile in boiling toluene gave the 7-azabicycloheptane 4a (a 5-exo cyclisation product) and the 8-azabicyclooctane 5a (a 6-endo product) (30percent), together with the reduction product 6a (12percent).The geriochemistry (5-exo/6-endo) of this cyclisation could be controlled by the introduction of a substituent on the prop-2-enyl group.The substituent(s) at the 2- and/or 4-position(s) of the pyrrolidine ring were found to play an important role in this cyclisation.
SYNTHESIS OF 7-AZABICYCLOHEPTANE AND 8-AZABICYCLOOCTANE SYSTEMS USING RADICAL CYCLIZATION
Sato, Tatsunori,Mori, Tomiyo,Sugiyama, Tadakatsu,Ishibashi, Hiroyuki,Ikeda, Masazumi
, p. 245 - 248 (2007/10/02)
A new method for the synthesis of the titled systems using cyclization of the α-acylamino radicals generated from methyl N-(o-bromobenzoyl)-2-(prop-2-enyl)pyrrolidine-2-carboxylates and the piperidine congener by Bu3SnH-mediated radical translocation reaction is described.
A NEW SYNTHETIC ROUTE TO TROPANE ALKALOIDS. PSEUDOTROPINE AND TROPACOCAINE
Iida, Hideo,Watanabe, Yohya,Kibayashi, Chihiro
, p. 5091 - 5094 (2007/10/02)
Pseudotropine and tropacocaine have been synthesized by a facile route involving the nitroso cycloaddition followed by internal SN2 displacement.