Chemistry of 1,2,5-thiadiazoles. III. [1,2,5]thiadiazolo[3,4-c][1,2,5]thiadiazole

Komin, Andrew P.; Street, R. W.; Carmack, Marvin

doi:10.1021/jo00907a009

Cited by 60 publications

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References 6 publications

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“…Our strategy for the synthesis of the desired Q and BTD compounds involved the treatment of commercially available o ‐phenylenediamine ( 1 ) with freshly distilled thionyl chloride in the presence of triethylamine in CH 2 Cl 2 as the solvent to afford 2,1,3‐benzothiadiazole ( 2 ) in 93 % yield after steam distillation 23–25. The reaction of 2 with molecular bromine (added dropwise very slowly) in hydrobromic acid exclusively affords 4,7‐disubstituted regioisomer 3 in 95 % yield (Scheme ) 26…”

Section: Resultsmentioning

confidence: 99%

Are Molecular 5,8‐π‐Extended Quinoxaline Derivatives Good Chromophores for Photoluminescence Applications?

et al. 2006

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The synthesis of a new series of photoluminescent compounds, namely 5,8-diaryl quinoxaline derivatives (aryl = phenyl, 4-fluorophenyl, 4-methoxyphenyl, and 4-cyanophenyl), was achieved by a direct Suzuki cross-coupling reaction with the employment of a NCP-pincer palladacycle. The electrochemical and photophysical properties of these compounds were also investigated. Four new 4,8-diaryl-2,1,3-benzothiadiazoles were also synthesized in order to enable a comparison between the two types of nitrogen-containing π-extended heterocycles. The substitution of a hydrogen atom at the 4-position of the aryl that is groups attached to the quinoxaline or benzothiadiazole base by either elec-

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Section: Resultsmentioning

confidence: 99%

Are Molecular 5,8‐π‐Extended Quinoxaline Derivatives Good Chromophores for Photoluminescence Applications?

et al. 2006

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“…

The compounds 5,6-dihydro-4H-imidazo [4,5-c] [1,2,5]oxadiazole (3a, R=H), 4,6,10,12-tetramethyl-5,6,11,12-tetrahydro-4H,10H-bis(1,2,5)oxadiazolo [3,4-d:3',4'-I] [1,3,6,8]tetraazecine (4b, R=CH 3 ), N 3 ,N 3 'methylenebis-3,4-diamino-1,2,5-oxadiazole (5a, R=H) and N 3 ,N 3 '-methylenebis(N,N'-dimethyl-3,4-diamino-1,2,5-oxadiazolee) (5b, R=CH 3 ) were synthesized from the reaction of formaldehyde with 3,4diamino-1,2, 5-oxadiazole and N,N'-3,4-dimethylamino-1,2,5-oxadiazole in an acetonitrile. J. Heterocyclic Chem., 44, 717 (2007).3,4-Diamino-1,2,5-oxadiazole derivatives (1) have been used for the preparation of the small ring high nitrogen heterocycles which are known as important starting materials for energetic compounds [1][2][3][4][5]. As reported by Willer and co-workers, the reaction of 1a with glyoxal leads to compound 2 [6].

…”

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confidence: 99%

“…The compounds 5,6-dihydro-4H-imidazo [4,5-c] [1,2,5]oxadiazole (3a, R=H), 4,6,10,12-tetramethyl-5,6,11,12-tetrahydro-4H,10H-bis(1,2,5)oxadiazolo [3,4-d:3',4'-I] [1,3,6,8]tetraazecine (4b, R=CH 3 ), N 3 ,N 3 'methylenebis-3,4-diamino-1,2,5-oxadiazole (5a, R=H) and N 3 ,N 3 '-methylenebis(N,N'-dimethyl-3,4-diamino-1,2,5-oxadiazolee) (5b, R=CH 3 ) were synthesized from the reaction of formaldehyde with 3,4diamino-1,2, 5-oxadiazole and N,N'-3,4-dimethylamino-1,2,5-oxadiazole in an acetonitrile. J. Heterocyclic Chem., 44, 717 (2007).…”

mentioning

confidence: 99%

“…3,4-Diamino-1,2,5-oxadiazole derivatives (1) have been used for the preparation of the small ring high nitrogen heterocycles which are known as important starting materials for energetic compounds [1][2][3][4][5]. As reported by Willer and co-workers, the reaction of 1a with glyoxal leads to compound 2 [6].…”

mentioning

confidence: 99%

“…The compounds 5,6-dihydro-4H-imidazo [4,5-c] [1,2,5]oxadiazole (3a, R=H), 4,6,10,12-tetramethyl-5,6,11,12-tetrahydro-4H,10H-bis (1,2,5)oxadiazolo [3,4- 3,4-Diamino-1,2,5-oxadiazole derivatives (1) have been used for the preparation of the small ring high nitrogen heterocycles which are known as important starting materials for energetic compounds [1][2][3][4][5]. As reported by Willer and co-workers, the reaction of 1a with glyoxal leads to compound 2 [6].…”

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Reaction of 3,4‐Diamino‐1,2,5‐oxadiazoles with Formaldehyde.

et al. 2007

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DFT- and post-HF-study on structure and electronic excitation of acyclic and cyclic sulfur diimides

Straßner

Fabian

1997

J. Phys. Org. Chem.

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A series of representative organic acyclic and cyclic sulfur diimides were studied by Hartree–Fock‐plus‐correlation ab initio quantum chemistry and by density functional theory using Becke's three‐parameter functional along with the LYP functional. The widely used formula representation –NSN– for these compounds suggests octet expansion of sulfur. This is not confirmed by theory. Although d‐polarization functions significantly improve the numerical results, sulfur d‐orbitals are hardly occupied. The calculated electronic charge distribution derived by population analysis and by the atoms‐in‐molecules topological theory favors charge separation resulting in a more or less ylidic structure with –NS+–N−– and –N−=S+–N– resonance contributors. This structure does not exclude relatively short SN bond lengths. The characteristics of the bonds in the parent structures is preserved in some non‐Kekulé‐type NSN heterocyles. Strong SN bond charge separations of organyl sulfur diimides are accompanied by short SN bond distances and narrow S0/T1 and S0/S1 energy gaps. The experimentally well known naphtho[1,8‐cd][1,2,6]thiadiazine and the unknown 3,4‐dimethylene‐1,2,5‐thiadiazole belong to this series. The calculations confirm that 1,2,3‐thiadiazole is the diaza analog of thiophene rather than the vinylene‐bridged sulfur diimide, while more complex heterocycles such as benzo[1,2‐c;4,5‐c′]bis[1,2,5]thiadiazole take an intermediate position between classical and non‐classical structures. Two closely related minimum structures are defined on the DFT Born–Oppenheimer energy surface of naphtho[1,8‐cd;4,5‐c′d′]bis[1,2,6]thiadiazine, but so far only one compound is experimentally known. The lowest energy structure is the quinoid form corresponding to the experimentally known compound. © 1997 John Wiley & Sons, Ltd.

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Chemistry of 1,2,5-thiadiazoles. III. [1,2,5]thiadiazolo[3,4-c][1,2,5]thiadiazole

Cited by 60 publications

References 6 publications

Are Molecular 5,8‐π‐Extended Quinoxaline Derivatives Good Chromophores for Photoluminescence Applications?

Are Molecular 5,8‐π‐Extended Quinoxaline Derivatives Good Chromophores for Photoluminescence Applications?

Reaction of 3,4‐Diamino‐1,2,5‐oxadiazoles with Formaldehyde.

DFT- and post-HF-study on structure and electronic excitation of acyclic and cyclic sulfur diimides

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