Cyclizations and rearrangements of propynylsulfamides: x-ray crystal structure of 2,3-dihydro-2-acetyl-3,3-dimethyl-4-[(1E)-4-methyl-1,3-pentadienyl]-1,2,5-thiadiazole 1,1-dioxide

Baker, Ronald J.; Chiu, Sai-Keung; Klein, Cheryl L.; Timberlake, Jack W.; Trefonas, L. M.; Majeste, R. J.

doi:10.1021/jo01291a021

Cited by 12 publications

(4 citation statements)

References 2 publications

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“…The C=N bond distances are 1.289(2) and 1.285(2) Å in 4 and 1.293(4) and 1.296(4) Å in 5, which are also in close agreement with previous determinations. [9][10][11] As expected, the heterocyclic ring is planar, within experimental error (rms deviation of ring atoms from the mean plane is less than 0.012 Å for 4 and less than 0.008 Å for 5). Single crystals were obtained by slow evaporation of the solvent from MeCN solutions.…”

Section: Methodssupporting

confidence: 83%

Efficient Formation of Polycyclic Aromatic Systems Fused to a Thiadiazole Ring Using Strong Lewis or Brønsted Acids

Svartman¹,

Rozas²,

Piro³

et al. 2006

Synthesis

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We report the efficient formation of a 9,10-dihydrophenanthrene polycyclic system fused to 1,2,5-thiadiazole 1,1-dioxide via formation of an aryl-aryl bond using strong Brønsted and Lewis acids, at different temperatures. The syntheses of the novel asymmetric 3,6-dibenzophenanthro[9,10-c]-and phenanthro[9,10-c]-1,2,5-thiadiazole 1,1-dioxides employing concentrated sulfuric or chlorosulfonic acids, or aluminum chloride as promoters are compared. The cyclizations promoted by Brønsted acids are faster than those with aluminum chloride, but the yields are similar. On a laboratory scale the cost of reagents using Brønsted acids is one half that for the conventional procedure. The preparation and characterization of 3,4-bis (2-naphthyl)-1,2,5-thiadiazole 1,1-dioxide, the precursor of the new asymmetric 3,6-dibenzophenanthro derivative, are also described, and some aspects of its cyclization are rationalized by inspection of the results of a PM3 geometry optimization.

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Section: Methodssupporting

confidence: 83%

Efficient Formation of Polycyclic Aromatic Systems Fused to a Thiadiazole Ring Using Strong Lewis or Brønsted Acids

Svartman¹,

Rozas²,

Piro³

et al. 2006

Synthesis

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show abstract

“…The structural details in Tables 5-7 allow comparisons among these compounds and with reported studies on related compounds, such as thiadiazines, 24-28 a thiadiazoline, 29 a thiadiazole 1-dioxide 30 and a thiadiazole, 31 and suggest relationships with their experimental chemical behavior that will be discussed below.…”

Section: Results and Discussion Crystallographymentioning

confidence: 99%

Crystallographic study and molecular orbital calculations of 1,2,5-thiadiazole 1,1-dioxide derivatives

Castellano

Piro

Caram

et al. 1998

J. Phys. Org. Chem.

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Single-crystal x-ray diffraction studies are reported for 3,4-dimethyl (I), 3-methyl-4-phenyl (II) and 3,4-diphenyl (III) derivatives of 1,2,5-thiadiazole 1,1-dioxide. Ab initio MO calculations on the electronic structure, conformation and reactivity of I, II and III are also reported and compared with the x-ray results. The structural data are related to previous kinetic and electrochemical experimental results on these compounds.

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“…The structural assignment to adducts 11a-c was unequivocally established by 1 H-NMR spectroscopy, since the absence of vicinal coupling constants between protons H-1 and H-2 as well as between protons H-3 and H-4 (Scheme 1) is a clear indication of their exo configuration. 49,50 By taking into account the outcome of reactions carried out on olefins structurally related to 8, 51,52 we assigned the exo configuration even to spirocyclic intermediates 9a-c, which were the only isomers isolated in each cycloaddition step. Finally, the pericyclic reaction of pyridinenitrile oxides with olefin 12 yielded bicyclic cycloadducts 13a-c.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of novel epibatidine-related derivatives through 1,3-dipolar cycloaddition of pyridinenitrile oxides

Dallanoce¹,

Bazza²,

Grazioso³

et al. 2006

Arkivoc

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The ∆ 2 -isoxazoline derivatives 3a-c and 4a-c, structurally related to epibatidine, and the simplified analogues 5a-c were synthesized by means of a 1,3-dipolar cycloaddition of regioisomeric pyridinenitrile oxides to suitable dipolarophiles. Target compounds were assayed at α4β2 and α7 neuronal acetylcholine receptor (nAChR) subtypes. Competition binding experiments at α4β2 nAChRs showed an overall significant reduction in affinity for the compounds under study in comparison to the reference radioligand [ 3 H]-epibatidine. On the other hand, compounds 3b, 3c, and 4b exhibited a noticeable affinity for the α7 receptors and 3c showed also a slight degree of α7 over α4β2 selectivity.

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Cyclizations and rearrangements of propynylsulfamides: x-ray crystal structure of 2,3-dihydro-2-acetyl-3,3-dimethyl-4-[(1E)-4-methyl-1,3-pentadienyl]-1,2,5-thiadiazole 1,1-dioxide

Cited by 12 publications

References 2 publications

Efficient Formation of Polycyclic Aromatic Systems Fused to a Thiadiazole Ring Using Strong Lewis or Brønsted Acids

Efficient Formation of Polycyclic Aromatic Systems Fused to a Thiadiazole Ring Using Strong Lewis or Brønsted Acids

Crystallographic study and molecular orbital calculations of 1,2,5-thiadiazole 1,1-dioxide derivatives

Synthesis of novel epibatidine-related derivatives through 1,3-dipolar cycloaddition of pyridinenitrile oxides

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