An improved procedure for the synthesis of 4,4‐disubstituted‐3‐oxo‐1,2,5‐thiadiazolidine 1,1 ‐dioxides

Xiao, Zejun; Timberlake, Jack W.

doi:10.1002/jhet.5570370418

Cited by 26 publications

(25 citation statements)

References 21 publications

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“…For related literature, see: Berredjem et al (2000); Lee & Lee (2002); Martinez et al (2000); Xiao & Timberlake (2000); Esteve & Bidal (2002); Soledade et al (2006).…”

Section: Related Literaturementioning

confidence: 99%

1,2,3,4-Tetrahydroisoquinoline-2-sulfonamide

et al. 2008

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The title compound, C9H12N2O2S, is a useful precursor of a variety of modified sulfonamide molecules. Due to the importance of these molecules in biological systems (antibacterials, antidepressants and many other applications), there is a growing interest in the discovery of new biologically active compounds. In the title compound, the molecules are linked by N—H⋯O intermolecular hydrogen bonds involving the sulfonamide function to form an infinite two-dimensional network parallel to the (001) plane.

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“…For related literature, see: Berredjem et al (2000); Lee & Lee (2002); Martinez et al (2000); Xiao & Timberlake (2000); Esteve & Bidal (2002); Soledade et al (2006).…”

Section: Related Literaturementioning

confidence: 99%

1,2,3,4-Tetrahydroisoquinoline-2-sulfonamide

et al. 2008

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“…Based on IR collections [15], literature references [16][17][18], and in the many thiadiazole 1,1-dioxide derivatives IR spectra measured in our laboratory [9,12,19,20], these characteristic IR bands were assigned as indicated in the second column of Table I. As it is known, IR frequencies calculated using HF model chemistries are higher than the actual ones. The difference is systematic [21] and the accuracy can be increased enormously using a constant scaling factor, which, for HF/6-31G(d), is 0.8953 [22].…”

Section: Resultsmentioning

confidence: 99%

On experimental versus theoretically calculated properties of thiadiazole derivatives

Vasini

Mirífico

Caram

2011

Int J of Quantum Chemistry

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ABSTRACT:The recently published results of a theoretical calculation of the physicochemical properties of acenaphtho[1,2-c]-and phenanthro[9,10-c]-1,2,5-thiadiazole 1,1-dioxide, using a modified density functional theory (CHIH-DFT), are compared with our experimental results. The CHIH-DFT-calculated IR spectra of both compounds are also compared with those obtained using relatively simple RHF calculations. It is concluded that, in these cases, the improvements claimed for the new model chemistry are marginal. The IR spectra of three new derivatives of 1,2,5-thiadiazole are also reported and calculated.

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“…Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 Sulfonamides are an important category of pharmaceutical compounds with a broad spectrum of biological activities such as herbicidal, anti-malarial, anti-convulsant and anti-hypertensive (Connor, 1998;Xiao & Timberlake, 2000;Berredjem et al, 2000;Lee & Lee, 2002). In this work we report the crystal structure of the title compound (Fig 1, Alternative name: 2-tosylaminobenzaldehyde), which is the second monoclinic polymorph reported.…”

Section: Methodsmentioning

confidence: 99%

“…For biological applications of sulfonamides, see: Connor (1998); Berredjem et al (2000); Lee & Lee (2002); Xiao & Timberlake (2000). For the first monoclinic polymorph, see: Mahía et al (1999).…”

Section: Related Literaturementioning

confidence: 99%

N-(2-Formylphenyl)-4-toluenesulfonamide: a second monoclinic polymorph

Murugavel¹,

Manikandan²,

Kannan³

et al. 2012

Acta Cryst E

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The title compound, C14H13NO3S, (I), is a second monoclinic polymorph. The original polymorph, (II), was reported by Mahía et al. [Acta Cryst. (1999), C55, 2158–2160]. Polymorph (II) crystalllized in the space group P21/c (Z = 4), whereas the title polymorph (I) occurs in the space group P21/n (Z = 4). The dihedral angle between the two aromatic rings is 75.9 (1)° in (I) compared to 81.9 (1)° for (II). In both polymorphs, two S(6) rings are generated by intramolecular N—H⋯O and C—H⋯O hydrogen bonds, resulting in similar molecular geometries. However, the two polymorphs differ concerning their crystal packing. In (I), molecules are linked into C(8) zigzag chains along the b axis by C—H⋯O hydrogen bonds, whereas in (II) molecules are linked by C—H⋯O hydrogen bonds, forming C(7) chains along the b axis. The title polymorph is further stabilized by intermolecular C—H⋯π and π–π interactions [centroid–centroid distance = 3.814 (1) Å]. These interactions are not evident in polymorph (II).

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An improved procedure for the synthesis of 4,4‐disubstituted‐3‐oxo‐1,2,5‐thiadiazolidine 1,1 ‐dioxides

Abstract: An improved synthesis for the preparation of 3‐oxo‐1,2,5‐thiadiazolidine 1,1‐dioxides has been developed. This facile two‐step procedure fromα‐amino acid esters and chlorosulfonyl isocyanate results in excellent yields of products.

Cited by 26 publications

References 21 publications

1,2,3,4-Tetrahydroisoquinoline-2-sulfonamide

1,2,3,4-Tetrahydroisoquinoline-2-sulfonamide

On experimental versus theoretically calculated properties of thiadiazole derivatives

N-(2-Formylphenyl)-4-toluenesulfonamide: a second monoclinic polymorph

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