7-Substituted benzo[b]thiophenes and 1,2-benzisothiazoles. Part 1. Hydroxy- or methoxy-derivatives

Rahman, Loay K. A.; Scrowston, R. M.

doi:10.1039/p19830002973

Cited by 40 publications

(18 citation statements)

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“…43 The more challenging example of substituted 7-hydroxybenzo [b]thiophene and its derivatives was accomplished via NKR, providing sulfur isosteres 32 of biologically active hydroxyindoles (Scheme 18). 44 This approach proceeded through 2-mercapto-3-methoxybenzaldehyde (33) which also provided access to 7-substituted 1,2-benzisothiazoles 34. The substitution patterns on both these heterocycles had been difficult to achieve by other methods.…”

Section: General Routes To Ar-shmentioning

confidence: 99%

Mechanism and Application of the Newman-Kwart O→S Rearrangement of O-Aryl Thiocarbamates

Lloyd‐Jones¹,

Moseley²,

Renny³

2008

Synthesis

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This literature review focuses on the thermal rearrangement of O-aryl thiocarbamates to yield the corresponding S-aryl thiocarbamates: the Newman-Kwart rearrangement. The purpose of the review is to highlight the utility of the rearrangement which provides a key step in an efficient route to convert phenols into thiophenols. The scope of the Newman-Kwart rearrangement is illustrated by way of numerous examples of its application to the preparation of Ar-S species ranging from large-scale industrial processes through to the synthesis of complex organic molecules such as ligands and supramolecular structures. The review contains 238 references and covers just over 40 years of the literature, from the first reports of the rearrangement by Edwards and Pianka in 1965 up to mid-2007. 1 Introduction 2 The Newman-Kwart Rearrangement (NKR) 2.1 Background and History 2.2 Preparation of O-Aryl Thiocarbamates for NKR and Subsequent Cleavage 2.3 Mechanism of Rearrangement 2.4 Nonclassical Conditions for Rearrangement 2.5 Allylic and Benzylic Rearrangements 2.

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Section: General Routes To Ar-shmentioning

confidence: 99%

Mechanism and Application of the Newman-Kwart O→S Rearrangement of O-Aryl Thiocarbamates

Lloyd‐Jones¹,

Moseley²,

Renny³

2008

Synthesis

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“…Several pyrazines [ 373 , 374 , 375 , 376 , 377 , 378 , 379 , 380 , 381 ], oxazines [ 382 , 383 , 384 , 385 ], and thiazines [ 386 , 387 , 388 , 389 , 390 , 391 , 392 , 393 ] were obtained when 177 were treated with α-haloketones ( Scheme 51 ).…”

Section: Reactions Of α-Haloketones With Oxygen Nitrogen and Sulfmentioning

confidence: 99%

The Chemistry of α-Haloketones and Their Utility in Heterocyclic Synthesis

2003

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“…The synthesis of α‐thio‐substituted glycine from the corresponding α‐acetoxyglycine was performed using the strategy described by Kingsbury et al8 The key step (Scheme ) in the syntheses of the α‐[(difluoromethyl)arylthio]glycines 12 , 13 and 14 resides in the substitution of the acetoxy group of the racemic pseudodipeptide 2 7 by the corresponding thio‐substituted benzaldehydes 3 , 4 and 5 . Compounds 3 and 4 were obtained by the Newman−Kwart rearrangement11,12 of O ‐dimethylthiocarbamoylated vanillin9 and ortho ‐vanillin,10 respectively. 2‐Thiosalicylaldehyde ( 5 ) was conveniently synthesized in 32% yield by formylation of the thiophenol dilithium salt 13,14.…”

Section: Resultsmentioning

confidence: 99%

“…α‐Acetoxyglycine ( 2 ) was synthesized as described earlier 7. 4‐Mercapto‐3‐methoxybenzaldehyde ( 3 ),9,11,12 2‐mercapto‐3‐methoxybenzaldehyde ( 4 ),10−12 and 2‐thiosalicylaldehyde ( 5 )13,14 were prepared according to literature methods.…”

Section: Methodsmentioning

confidence: 99%

Design and Evaluation of Mechanism-Based Inhibitors of D-Alanyl-D-alanine Dipeptidase VanX

et al. 2002

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VanX protein is a D‐alanyl‐D‐alanine dipeptidase essential for vancomycin resistance in Enterococcus. It is also a key drug target in circumventing clinical glycopeptide antibiotic resistance. The dipeptide‐like compound D‐Ala‐D‐Gly(SC6H4‐p‐CHF2) (1) was recently reported as the first mechanism‐based inhibitor with high affinity for the enzyme but poor inhibitory efficiency (kinact/Kirr = 9320 M−1 s−1) and a high partition ratio (7600). In order to assess the effects of variations in aromatic substituents on the in vitro inhibition properties of 1, we have prepared a few derivatives and analyzed them using the alternative substrate D‐Ala‐D‐Gly(SPh)‐OH (15) designed according to a similar strategy. Whereas moving the electrophilic difluoromethyl group to the ortho position slightly improved the inhibition parameters (kinact/Kirr = 1140 M−1 s−1) with a small decrease in the partition ratio (7200), introduction of a methoxy group in D‐Ala‐D‐ortho/para‐(difluoromethyl)phenylthioglycines resulted in a marked decrease in inhibitory efficiency. These results demonstrate the difficulties in improving the leading compound 1 given the restricted space available at the VanX active site. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)

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7-Substituted benzo[b]thiophenes and 1,2-benzisothiazoles. Part 1. Hydroxy- or methoxy-derivatives

Cited by 40 publications

References 0 publications

Mechanism and Application of the Newman-Kwart O→S Rearrangement of O-Aryl Thiocarbamates

Mechanism and Application of the Newman-Kwart O→S Rearrangement of O-Aryl Thiocarbamates

The Chemistry of α-Haloketones and Their Utility in Heterocyclic Synthesis

Design and Evaluation of Mechanism-Based Inhibitors of D-Alanyl-D-alanine Dipeptidase VanX

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