A convenient one-pot synthesis of thiazol-2-imines: application in the construction of pifithrin analogues

Murru, Siva; Singh, Chingakham Brajakishor; Kavala, Veerababurao; Patel, Bhisma K.

doi:10.1016/j.tet.2007.11.076

Cited by 85 publications

(37 citation statements)

References 53 publications

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“…[6] Recently, we have reported several ligand-assisted Cu(I)-catalyzed syntheses of 2-mercaptobenzimidazoles, [7a] 2-substituted 1,3-benzothiazoles, [7b] and arylthiobenzothiazoles.…”

Section: Resultsmentioning

confidence: 99%

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Copper(I)‐Catalyzed Cascade Synthesis of 2‐Arylsulfanyl‐ arylcyanamides

et al. 2010

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Abstract:We have developed a ligand-assisted copper(I)-catalyzed two sequential heteroarylation sequence. An intramolecular S-arylation is followed by an intermolecular N-arylation leading to the direct synthesis of N-aryl-2-aminobenzothiazoles. In most cases however, the 2-arylsulfanyl-arylcyanamide was the major product obtained via an intramolecular C À S bond formation, associated with C À S bond breakage, followed by an intermolecular S-arylation. The selectivity of this ligand-assisted reaction is quite different as compared to that of ligand-free reactions and the rates are much faster giving good yields of products. Various cyanamides can be prepared in excellent yields from their corresponding 1-substituted thioureas with or without the assistance of a ligand with a catalytic quantity of copper(I).

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“…[6] Recently, we have reported several ligand-assisted Cu(I)-catalyzed syntheses of 2-mercaptobenzimidazoles, [7a] 2-substituted 1,3-benzothiazoles, [7b] and arylthiobenzothiazoles.…”

Section: Resultsmentioning

confidence: 99%

“…[1h] As a part of our ongoing research in developing alternative methods for the synthesis of heterocycles, [6,7] and taking cues from our recent double S-arylation strategy involving intra-and intermolecular C À S coupling, [1h] we envisaged a one-pot synthesis of N-aryl-2-aminobenzothiazoles. The retrosynthetic strategy is shown in Scheme 1.…”

Section: Resultsmentioning

confidence: 99%

Copper(I)‐Catalyzed Cascade Synthesis of 2‐Arylsulfanyl‐ arylcyanamides

et al. 2010

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“…[11][12][13][14][15][16][17] Significantly, the unique examples cited in literature of the use of 1,3-dichloroacetone with aromatic amines entail reactions with highly nucleophilic ambident amines (e.g., 2-aminopyridine). [18][19][20] (D) The activation of the carbonyl moiety by an acid allows the addition to the carbonyl carbon of a suitable nucleophile (hydroxylamine derivatives 21 or diols).…”

Section: Scheme 1 Abstractsmentioning

confidence: 99%

1,3-Dichloroacetone

Pace¹

2010

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“…4 The unsymmetrical thiourea gives a regioisomeric mixture of products and the regioselectivity is dependent on the pKa values of the corresponding amines attached to the thiourea moiety. 5 …”

Section: Scheme 1 Synthesis Of Symmetrical and Unsymmetrical Thioureasmentioning

confidence: 99%

1,3-Disubstituted Thioureas: Versatile Building Blocks for the Construction of Heterocycles

Ghosh¹

2009

Synlett

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This feature focuses on a reagent chosen by a postgraduate, highlighting the uses and preparation of the reagent in current research 1,3-Disubstituted Thioureas: Versatile Building Blocks for the Construction of Heterocycles Compiled by Harisadhan Ghosh Harisadhan Ghosh was born in Burdwan, West Bengal, India, in 1983. He received his B.Sc. (2004) and M. Sc. (2006) degrees in Organic Chemistry from Visva-Bharati University, Santiniketan, India. Currently he is carrying out his Ph.D thesis under the supervision of Prof. Bhisma K. Patel as a CSIR junior research fellow. His research interests focus on hypervalent iodine mediated organic synthesis.

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A convenient one-pot synthesis of thiazol-2-imines: application in the construction of pifithrin analogues

Cited by 85 publications

References 53 publications

Copper(I)‐Catalyzed Cascade Synthesis of 2‐Arylsulfanyl‐ arylcyanamides

Copper(I)‐Catalyzed Cascade Synthesis of 2‐Arylsulfanyl‐ arylcyanamides

1,3-Dichloroacetone

1,3-Disubstituted Thioureas: Versatile Building Blocks for the Construction of Heterocycles

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