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Reductive cyclization of carbohydrate 2‐nitrophenylhydrazones to chiral functionalized 1,2,4‐benzotriazines and benzimidazoles
Author(s) -
Andersch Jens,
Sicker Dieter
Publication year - 1999
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.5570360302
Subject(s) - chemistry , yield (engineering) , catalysis , amine gas treating , organic chemistry , arabinose , catalytic hydrogenation , aldose , carbohydrate , acetal , combinatorial chemistry , glycoside , materials science , xylose , fermentation , metallurgy
The 2‐nitrophenylhydrazones 2 of D‐ arabino ‐2‐hexulopyranosonic acid, D‐arabinose, D‐galactose and D‐galacturonic acid are used as precursors to form chiral functionalized 1,2,4‐benzotriazines and benzimidazoles by reductive cyclization methods. Catalytic hydrogenation provided the amine derivatives which are cyclized and air oxidized in alkaline solution to yield the novel 1,2,4‐benzotriazines 3 as the main products, while on acid catalysis the benzimidazoles 4 are formed.