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An Efficient and Tunable Route to Bis(1,2,3‐triazol‐1‐yl)methane‐Based Nitrogen Compounds
Author(s) -
CastroOsma José A.,
LaraSanchez Agustín,
Otero Antonio,
Rodríguez Ana M.,
de la Torre María C.,
Sierra Miguel A.
Publication year - 2016
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/ejoc.201501519
Subject(s) - chemistry , geminal , cycloaddition , methane , alkyne , nitrogen , azide , crystal structure , zinc , catalysis , click chemistry , organic chemistry , combinatorial chemistry , medicinal chemistry
Abstract A new and easy route to prepare “a la carte” bis(1,2,3‐triazol‐1‐yl)methane compounds, namely bmtzm ( 1 ), bptzm ( 2 ), bttzm ( 3 ), bmtzpm ( 4 ), bptzpm ( 5 ), bttzpm ( 6 ), bmtzom ( 7 ), bptzom ( 8 ) and bttzom ( 9 ), with different functional groups is reported. The compounds were prepared by reaction between readily accessible alkynes and geminal diazides in a double Cu‐catalyzed azide‐alkyne cycloaddition (CuAAC) reaction. These materials were used as starting materials for the synthesis of more elaborate compounds. Thus, the preparation of new bis(1,2,3‐triazol‐1‐yl)methane‐based heteroscorpionate neutral precursors pbptztamH ( 10 ), pbttztamH ( 11 ), ( S )‐mbptzamH ( 12 ) and ( S )‐mbttzamH ( 13 ) and a dinuclear zinc complex, [Zn{pbptztam}Et] 2 ( 14 ), was achieved. The structures of the compounds were determined by spectroscopic methods, and the X‐ray crystal structures of compounds 2 , 3 , 7 , 8 , 9 and 14 were established.