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Facile preparation of 7,11‐di(4‐nitrobenzenesulfonyl)‐diaza‐1,4‐dioxa‐7,11‐spiro[4,7]dodecan‐9‐one
Author(s) -
Park YoungDae,
Cho SuDong,
Kim JeumJong,
Kim HoKyun,
Kweon DeokHeon,
Lee SangGyeong,
Yoon YongJin
Publication year - 2006
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570430242
Subject(s) - chemistry , yield (engineering) , ketone , chromic acid , medicinal chemistry , organic chemistry , metallurgy , materials science
Compound 1 as a key intermediate for the synthesis of 3,3,7,7‐tetrakis‐(difluoroamino)octahydro‐1,5‐dinitro‐1,5‐diazocine (HNFX) and 3,3‐bis(difluoroamino)octahydro‐1,5,7,7‐tetranitro‐1,5‐diazocine (TNFX) is described. Cycloalkylation of 3 with 1,3‐dibromopropan‐2‐ol ( 4 ) afforded 1,5‐protected‐1,5‐diazocine 2 , followed by chromic acid oxidation to ketone 1 in good yield.