Journal of Organic Chemistry p. 4428 - 4438 (1995)
Update date:2022-08-05
Topics:
Arunachalam, T.
Fan, H.
Pillai, K. M. R.
Ranganathan, R. S.
Intramolecular iodocyclization of ω-alkenylanilides 6 and <ω-(alkenyloxy)alkyl>anilides 7 resulted in the formation of dihydro-2(3H)-furanylidenamines 8 and 1,4-dioxan-2-ylideneamines 9, respectively, by an amide-oxygen participative nucleophilic attack on the expected iodonium intermediate.The latter heterocyclic ring system is new.If a strong base is present, the mode of ring closure was mainly diverted to an amide-nitrogen participative nucleophilic attack, leading to (iodomethyl)pyrrolidinones 10 and (iodomethyl)morpholinones 11, from 6 and 7, respectively.Unique interconvertible syn-anti isomerism in the imino-ether 8a was demonstrated by variable temperature NMR studies.The major component in this mixture was the 8a-anti-isomer.Acetolysis of the iodocyclized products, followed by deacetylation, provided the heterocyclically substituted polyhydroxytriiodoisophthalamides 16-18.Hydrolytic studies on the imidate 16d revealed an interesting pH dependence.As expected the amine 3d and the amide 22 resulted in pH values of 2 and 6.At pH 12, however, the Chapman rearrangement product 17d was the major product.The compounds obtained in this investigation are of interest as X-ray contrast agents.
View MoreChengdu Gelipu Biotechnology Co., Ltd.
website:http://www.glp-china.com
Contact:86-28-82610909
Address:chegndu
Changsha Huajing Powdery Material Technological Co., Ltd.
Contact:86-731-88879686
Address:Building 2, West Garden, Main Campus of Central South University, Changsha, Hunan Province, China
Hunan Dinuo Pharmaceutical Co.,Ltd.
Contact:86-731-88280100*8561
Address:Bio-pharmaceutical industrial park, Liuyang, Hunan, China
Changzhou Ansciep Chemical Co.,Ltd.
Contact:+86 519 8630 5871
Address:A-710 Boan International, 8 East Guangdian Road,Wujin,Changzhou
Suzhou Chiral Pharmaceuticals Co., Ltd.
Contact:86-0512-63197058
Address:Building A, No. 2358, Chang'an Road, Wujiang Science Park
Doi:10.1021/jo01271a026
(1968)Doi:10.1002/jps.2600841003
(1995)Doi:10.1016/0960-894X(96)00148-5
(1996)Doi:10.1021/ja00133a010
(1995)Doi:10.1039/DT9960004633
(1996)Doi:10.1021/ja00112a007
(1995)