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Reactions between arylhydrazinium chlorides and 2‐chloroquinoline‐3‐carbaldehydes: molecular and supramolecular structures of a hydrazone, a 4,9‐dihydro‐1 H ‐pyrazolo[3,4‐ b ]quinoline and two 1 H ‐pyrazolo[3,4‐ b ]quinolines
Author(s) -
Kumara Tholappanavara H. Suresha,
Nagendrappa Gopalpur,
Chandrika Nanjappa,
Sowmya Haliwana B. V.,
Kaur Manpreet,
Jasinski Jerry P.,
Glidewell Christopher
Publication year - 2016
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s205322961601278x
Subject(s) - quinoline , chemistry , hydrazone , hydrogen bond , molecule , medicinal chemistry , stereochemistry , sodium cyanoborohydride , organic chemistry
Hydrazone derivatives exhibit a wide range of biological activities, while pyrazolo[3,4‐ b ]quinoline derivatives, on the other hand, exhibit both antimicrobial and antiviral activity, so that all new derivatives in these chemical classes are potentially of value. Dry grinding of a mixture of 2‐chloroquinoline‐3‐carbaldehyde and 4‐methylphenylhydrazinium chloride gives ( E )‐1‐[(2‐chloroquinolin‐3‐yl)methylidene]‐2‐(4‐methylphenyl)hydrazine, C 17 H 14 ClN 3 , (I), while the same regents in methanol in the presence of sodium cyanoborohydride give 1‐(4‐methylphenyl)‐4,9‐dihydro‐1 H ‐pyrazolo[3,4‐ b ]quinoline, C 17 H 15 N 3 , (II). The reactions between phenylhydrazinium chloride and either 2‐chloroquinoline‐3‐carbaldehyde or 2‐chloro‐6‐methylquinoline‐3‐carbaldehyde give, respectively, 1‐phenyl‐1 H ‐pyrazolo[3,4‐ b ]quinoline, C 16 H 11 N 3 , (III), which crystallizes in the space group Pbcn as a nonmerohedral twin having Z ′ = 3, or 6‐methyl‐1‐phenyl‐1 H ‐pyrazolo[3,4‐ b ]quinoline, C 17 H 13 N 3 , (IV), which crystallizes in the space group R . The molecules of compound (I) are linked into sheets by a combination of N—H…N and C—H…π(arene) hydrogen bonds, and the molecules of compound (II) are linked by a combination of N—H…N and C—H…π(arene) hydrogen bonds to form a chain of rings. In the structure of compound (III), one of the three independent molecules forms chains generated by C—H…π(arene) hydrogen bonds, with a second type of molecule linked to the chains by a second C—H…π(arene) hydrogen bond and the third type of molecule linked to the chain by multiple π–π stacking interactions. A single C—H…π(arene) hydrogen bond links the molecules of compound (IV) into cyclic centrosymmetric hexamers having ( S 6 ) symmetry, which are themselves linked into a three‐dimensional array by π–π stacking interactions.