S-arylation of mercaptobenzimidazoles using Cu(I) catalysts—experimental and theoretical observations

Ramkumar, S. Manian; Marutheeswaran, S.; Marcelis, Antonius T. M.; Anandan, Sambandam

doi:10.1016/j.tetlet.2011.04.078

Cited by 29 publications

(27 citation statements)

References 40 publications

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“…For general background to spiranes, see: Dawood & AbdelWahab (2010); Dolbier et al (1994); Mavrova et al (2010); Sekar et al (2011). Table 1 Hydrogen-bond geometry (Å , ).…”

Section: Related Literaturementioning

confidence: 99%

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3-Fluoro-12H-benzimidazo[2,1-b][1,3]benzothiazin-12-one

Wang

Zhang

et al. 2012

Acta Cryst E

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In the title compound, C14H7FN2OS, prepared by the reaction of 2-bromo-4-fluorobenzoyl choride with 2-mercaptobenzimidazole, the four-membered fused-ring system is essentially planar [maximum deviation from the mean plane = 0.035 (2) Å]. The crystal packing is stabilized by weak intermolecular π–π [minimum ring centroid–centroid separation = 3.509 (7) Å], weak C—F⋯π [F⋯centroid = 3.4464 (17) Å, C—F⋯centroid = 97.72 (11)°] and C—O⋯π [O⋯centroid = 3.5230 (16) and 3.7296 (17) Å, C—O⋯centroid = 86.40 (10) and 86.25 (10)°] interactions and weak intermolecular C—H⋯N hydrogen bonds.

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“…For general background to spiranes, see: Dawood & AbdelWahab (2010); Dolbier et al (1994); Mavrova et al (2010); Sekar et al (2011). Table 1 Hydrogen-bond geometry (Å , ).…”

Section: Related Literaturementioning

confidence: 99%

“…In the past decades, most of these investigations were carried out with imidazole derivatives (Dolbier et al, 1994;Sekar et al, 2011). We herein present the structure of the title compound C 14 H 7 FN 2 OS, prepared from the reaction of 2-bromo-4-fluorobenzoyl choride with 2-mercaptobenzimidazole.…”

Section: Commentmentioning

confidence: 99%

3-Fluoro-12H-benzimidazo[2,1-b][1,3]benzothiazin-12-one

Wang

Zhang

et al. 2012

Acta Cryst E

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“…12H 4,133.7,132.2,131.7,131.1,126.9,125.8,125.7,124.0,122.4,118.3,115.9;IR (neat) 4, 146.4, 142.5, 137.3, 134.9, 131.7, 131.1, 128.8, 125.7, 125.5, 123.9, 122.2, 118.3, 115.9, 20.9;IR (neat) ν: 3017, 2968IR (neat) ν: 3017, , 1685IR (neat) ν: 3017, , 1443IR (neat) ν: 3017, , 1341IR (neat) ν: 3017, , 1267 4, 158.7, 146.6, 142.6, 131.7, 126.9, 125.8, 123.9, 123.5, 123.3, 123.1, 118.3, 115.9, 112.8, 55.7;IR (neat) ν: 3018, 2968IR (neat) ν: 3018, , 1740IR (neat) ν: 3018, , 1444IR (neat) ν: 3018, , 1365IR (neat) ν: 3018, , 1226 4, 145.5, 142.5, 134.1, 133.4, 131.1, 130.8, 130.6, 127.1, 126.1, 124.4, 123.9, 118.6, 116.0;IR (neat) ν: 3019, 2922IR (neat) ν: 3019, , 2852IR (neat) ν: 3019, , 1740IR (neat) ν: 3019, , 1484IR (neat) ν: 3019, , 1348IR (neat) ν: 3019, , 1201 4,142.5,140.8,134.1,132.7,131.8,127.8,126.1,125.4,124.5,121.1,118.7,116.0;IR (neat) 158.9, 155.3, 154.3, 145.9, 142.7, 139.0, 131.5, 126.2, 124.4, 122.0, 120.0, 118.7, 115.8;IR (neat) ν: 3057, 2923IR (neat) ν: 3057...…”

Section: General Procedures For the Synthesis Of Compounds 3 Andmentioning

confidence: 99%

“…5, 147.6, 143.5, 142.6, 137.8, 132.2, 131.5, 131.0, 127.7, 126.5, 126.1, 124.8, 119.0, 115.9;IR (neat) ν: 3018, 2922IR (neat) ν: 3018, , 2852IR (neat) ν: 3018, , 1741IR (neat) ν: 3018, , 1439IR (neat) ν: 3018, , 1369IR (neat) ν: 3018, , 1212IR (neat) ν: 3018, , 1002 (d,J＝ 7.6 Hz,2H),2H),7.70 (t,J＝8.0 Hz,2H),7.64 (d,J＝8.0 Hz,1H),5H),7.30 (d,J＝8.0 Hz,1H),7.25 (d,J＝8.0 Hz,1H), 2.56 (s, 3H), 2.53 (s, 3H); 13 C NMR (CDCl 3 , 100 MHz) δ: 159. 4, 159.1, 145.9, 145.2, 142.7, 140.4, 135.8, 134.2, 133.6, 133.5, 132.4, 132.3, 131.8, 131.2, 131.1, 129.6, 127.0, 126.9, 126.8, 125.6, 125.3, 122.6, 118.3, 117.8, 116.0, 115.3, 21.7, 21.6;IR (neat) ν: 3017, 2919IR (neat) ν: 3017, , 1693IR (neat) ν: 3017, , 1474IR (neat) ν: 3017, , 1352 5,133.8,133.6,131.4,131.3,126.7,126.0,121.0,115.4;IR (neat) 140.7,138.8,135.2,132.8,131.6,127.5,125.5,119.5,115.6;IR (neat) 4...…”

Section: General Procedures For the Synthesis Of Compounds 3 Andmentioning

confidence: 99%

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Copper‐Catalyzed Cascade Acylation/Coupling Cyclization Process for the Synthesis of Polycyclic Fused Imidazo[2,1‐‐b][1,3]thiazinones

Wang¹,

Yu²,

Zhang³

et al. 2011

Chin. J. Chem.

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A new and efficient cascade synthesis of polycyclic fused imidazo[2,1-b][1,3]thiazinones has been developed. This protocol includes an intermolecular N-acylation followed by a copper-catalyzed intramolecular C-S coupling reaction. The methodology is applied to a wide range of 2-iodo, 2-bromo, and 2-chloro benzoyl chlorides to yield the polycyclic fused imidazo[2,1-b][1,3]thiazinones in good to excellent yields.

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Copper‐Mediated Tandem C(sp²)–H Sulfenylation and Annulation of Arenes with 2‐Mercaptoimidazoles: Regio‐ and Site‐selective Access to Polycyclic Fused Imidazo[2,1‐b][1,3]thiazinones

et al. 2016

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An efficient copper-mediated tandem C(sp 2 )-H sulfenylation anda nnulation of arenes with 2-mercaptoimidazoles to provide polycyclic fused imidazo[2,1-b][1,3]thiazinones has been developed. This tandem reactioni sl ikelyi nitiated by C(sp 2 )-H thiolation of benzamide with 2-mercaptoimidazole followed by intramolecular nucleophilic substitution of the amide carbonyl group.Anotable feature of this reactioni st hat it can afford rather complex products in as ingle synthesis step from easily accessible starting materials using amide-oxazoline as ar emovable bidentate directing group.A variety of benzamides and 2-mercaptoimidazoles bearing different substituents are compatible with this transformation.

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S-arylation of mercaptobenzimidazoles using Cu(I) catalysts—experimental and theoretical observations

Cited by 29 publications

References 40 publications

3-Fluoro-12H-benzimidazo[2,1-b][1,3]benzothiazin-12-one

3-Fluoro-12H-benzimidazo[2,1-b][1,3]benzothiazin-12-one

Copper‐Catalyzed Cascade Acylation/Coupling Cyclization Process for the Synthesis of Polycyclic Fused Imidazo[2,1‐‐b][1,3]thiazinones

Copper‐Mediated Tandem C(sp²)–H Sulfenylation and Annulation of Arenes with 2‐Mercaptoimidazoles: Regio‐ and Site‐selective Access to Polycyclic Fused Imidazo[2,1‐b][1,3]thiazinones

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S-arylation of mercaptobenzimidazoles using Cu(I) catalysts—experimental and theoretical observations

Cited by 29 publications

References 40 publications

3-Fluoro-12H-benzimidazo[2,1-b][1,3]benzothiazin-12-one

3-Fluoro-12H-benzimidazo[2,1-b][1,3]benzothiazin-12-one

Copper‐Catalyzed Cascade Acylation/Coupling Cyclization Process for the Synthesis of Polycyclic Fused Imidazo[2,1‐‐b][1,3]thiazinones

Copper‐Mediated Tandem C(sp2)–H Sulfenylation and Annulation of Arenes with 2‐Mercaptoimidazoles: Regio‐ and Site‐selective Access to Polycyclic Fused Imidazo[2,1‐b][1,3]thiazinones

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Copper‐Mediated Tandem C(sp²)–H Sulfenylation and Annulation of Arenes with 2‐Mercaptoimidazoles: Regio‐ and Site‐selective Access to Polycyclic Fused Imidazo[2,1‐b][1,3]thiazinones