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A new highly efficient method for the synthesis of trans ‐tetrahydro‐3,4‐furandiamine
Author(s) -
Bitha Panayota,
Lin YangI
Publication year - 1988
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.5570250363
Subject(s) - chemistry , yield (engineering) , ammonium hydroxide , aqueous solution , catalysis , base (topology) , sodium hydroxide , sodium nitrite , ammonium chloride , nitro , combinatorial chemistry , chloride , nitrite , selective catalytic reduction , organic chemistry , nitrate , mathematical analysis , materials science , alkyl , mathematics , metallurgy
A new four‐step, highly efficient synthesis of trans ‐tetrahydro‐3,4‐furandiamine is described. Nitromercuration of 2,5‐dihydrofuran with sodium nitrite and mercuric chloride in aqueous solution followed by base catalyzed elimination yielded 3‐nitro‐2,5‐dihydrofuran which was aminated with ammonium hydroxide to give trans ‐tetrahydro‐4‐nitro‐3‐furanamine. Catalytic reduction of this material afforded the desired product 5 in 37% overall yield.