Molecules 2006, 11(6), 444-452; doi:10.3390/11060444
Article

Synthesis, Molecular Structure and Characterization of Allylic Derivatives of 6-Amino-3-methyl-1,2,4-triazolo[3,4-f][1,2,4]-triazin-8(7H)-one

Received: 31 May 2006; in revised form: 17 June 2006 / Accepted: 19 June 2006 / Published: 22 June 2006
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Abstract: 1-Allyl- (2) and 7-allyl-6-amino-3-methyl-1,2,4-triazolo[3,4-f][1,2,4]triazin-8(7H)-one (3) were obtained via the 18-crown-6-ether catalyzed room temperature reactionof 6-amino-3-methyl-1,2,4-triazolo[3,4-f][1,2,4]triazin-8(7H)-one (1) with potassiumcarbonate and allyl bromide in dry acetone. The structures of these two derivatives wereverified by 2D-NMR measurements, including gHSQC and gHMBC measurements. Theminor compound 2 may possess aromatic character. A single crystal X-ray diffractionexperiment indicated that the major compound 3 crystallizes from dimethyl sulfoxide in themonoclinic space group P21/n and its molecular structure includes an attached dimethylsulfoxide molecule, resulting in the molecular formula C10H16N6O2S. Molecular structuresof 3 are linked by extensive intermolecular N-H···N hydrogen bonding [graph set C 1 (7)]. 1Each molecule is attached to the dimethyl sulfoxide oxygen via N-H···O intermolecularhydrogen bonding. The structure is further stabilized by π-π stacking interactions.
Keywords: 1; 2; 4-Triazine; 1; 2; 4-triazolo[3; 4-f][1; 2; 4]triazine; aromatic molecule; X-ray crystal structure; hydrogen bonds.
PDF Full-text Download PDF Full-Text [259 KB, uploaded 18 June 2014 19:27 CEST]

Export to BibTeX |
EndNote


MDPI and ACS Style

Hwang, L.-C.; Jane, S.-Y.; Lai, H.-Y.; Tu, C.-H.; Lee, G.-H. Synthesis, Molecular Structure and Characterization of Allylic Derivatives of 6-Amino-3-methyl-1,2,4-triazolo[3,4-f][1,2,4]-triazin-8(7H)-one. Molecules 2006, 11, 444-452.

AMA Style

Hwang L-C, Jane S-Y, Lai H-Y, Tu C-H, Lee G-H. Synthesis, Molecular Structure and Characterization of Allylic Derivatives of 6-Amino-3-methyl-1,2,4-triazolo[3,4-f][1,2,4]-triazin-8(7H)-one. Molecules. 2006; 11(6):444-452.

Chicago/Turabian Style

Hwang, Long-Chih; Jane, Shin-Yi; Lai, Hsing-Yi; Tu, Chun-Hsien; Lee, Gene-Hsiang. 2006. "Synthesis, Molecular Structure and Characterization of Allylic Derivatives of 6-Amino-3-methyl-1,2,4-triazolo[3,4-f][1,2,4]-triazin-8(7H)-one." Molecules 11, no. 6: 444-452.

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert