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3,6‐Bis(2 H ‐tetrazol‐5‐yl)‐1,2,4,5‐tetrazine: A Versatile Bifunctional Building Block for the Synthesis of Linear Oligoheterocycles
Author(s) -
Sauer Jürgen,
Pabst Gunther R.,
Holland Uwe,
Kim HyunSook,
Loebbecke Stefan
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200102)2001:4<697::aid-ejoc697>3.0.co;2-n
Subject(s) - tetrazine , chemistry , tetrazole , pyridazine , bifunctional , pyrrole , furan , ring (chemistry) , dibasic acid , thiophene , combinatorial chemistry , stereochemistry , organic chemistry , catalysis
3,6‐Bis(2 H ‐tetrazol‐5‐yl)‐1,2,4,5‐tetrazine ( 3 ) (BTT) is an energy‐rich compound and a strong dibasic acid. The bifunctional compound 3 is capable of [4+2] cycloadditions through its tetrazine unit as a 4π compound, and of acylating ring‐opening reactions through its tetrazole rings, leading to the formation of linear oligoheterocycles 7 , 12 with 1,2,4,5‐tetrazine, pyridazine, 1,3,4‐oxadiazole, thiophene, furan, and pyrrole units in sequences not easily available by other synthetic methods.