Helvetica Chimica Acta p. 521 - 530 (1988)
Update date:2022-07-30
Topics:
Ametamey, Simon M.
Hollenstein, Roger
Heimgartner, Heinz
The synthesis of 3-(dimethylamino)-2,2-dimethyl(1-15N)-2H-azirine (1*) was accomplished via reaction of 1-chloro-N,N,2-trimethyl-1-propenylamine (9) and sodium (1-15N) azide (Scheme 3).The earlier reported reactions of 1 with saccharin (10, Scheme 4), phthalimide (12, Scheme 5), and 2H-1,3-benzoxazin-2,4(3H)-dione (16, Scheme 6) were repeated with 1*, and the position of the 15N-label in the products was determined by 15N-NMR spectroscopy.Whereas the postulated reaction mechanismus for 10 and 12 were confirmed by those experiments, the mechanism for the reaction of 16 had to be revised.With respect to the position of 15N in the products 17 and 18, a new mechanism is formulated in Scheme 7.Treatment of 5,5-dimethyl-1,3-oxazolidine-2,4-dione (19) with 1* led to 3,4-dihydro-2H-imidazol-2-on 20 in which only N(3) was labelled.The mechanism of a ring expansion and transannular ring contraction as shown in Scheme 8 is in agreement with this finding.
View MoreDezhou Longteng Chemical Co., Ltd.
website:http://www.sodium-methoxide.cn/
Contact:0086-18866052283
Address:Xinhua Industrial Zone, Dezhou City, Shandong Province, China
Changzhou Baolong Chemical Industrial Co.,Ltd
website:http://www.czbaolong.com
Contact:0519-85720726 0519-85720721 13951213302
Address:No.1,Weihua Road,Xinbei District,Changzhou City,Jiangsu Province
Dalian Synco Chemical Co., Ltd.
Contact:+86-411-83635150
Address:Rm 1004, 24, Tangshan Street, Dalian
website:http://www.lonwinchem.com
Contact:Tel: 86-21-59858395
Address:No#966,Huaxu Road,Shanghai 201702,P.R.China
Lyrin Industrial Corporation Limited
Contact:86-731-82571800
Address:Rm 2408,Asia Economy International Building,Shaoshan Road South,Yuhua District,Changsha,Hunan,China
Doi:10.1007/s10593-015-1662-0
(2015)Doi:10.1021/acs.joc.7b03149
(2018)Doi:10.1039/DT9920001563
(1992)Doi:10.1021/ja01618a028
(1955)Doi:10.1021/ol503748t
(2015)Doi:10.1021/ja00468a018
(1977)