Solid-phase synthesis of 2-substituted-3-(substituted sulfanyl)-1,2,4-benzothiadiazine 1,1-dioxide library

Makino, Shingo; Okuzumi, Tatsuya; Nakanishi, Eiji; Tsuji, Takashi

doi:10.1016/s0040-4039(02)01862-2

Cited by 14 publications

(14 citation statements)

References 20 publications

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“…Although this method is not applicable to compound 3d, the corresponding compound 7 can be synthesized through an alternative solid-phase synthetic route. [7] CONCLUSIONS In conclusion, an efficient and flexible approach to various 4H-1,2,4-benzothiadiazine-1,1-dioxide derivatives was developed. The structural diversity of the title compounds is achieved by a two-step synthesis proceeding under mild conditions.…”

Section: Resultsmentioning

confidence: 96%

“…(%) for C 10 H 11 BrN 2 O 4 S 2 : C, 32.71; H, 3.02; Br,21.76;N,7.63. Found: C,32.52;H,3.09;Br,21.53;N,7.52. 8.60 (s,1 H,ArH).…”

Section: General Procedures For Preparation Of Sulfonylated Amidines (mentioning

confidence: 99%

“…(%) for C 10 H 10 Br 2 N 2 O 2 S: C,31.44;H,2.64;Br,41.38;N,7.33. Found: C,31.25;H,2.59;Br,41.72;N,7.28.…”

Section: General Procedures For Preparation Of Sulfonylated Amidines (mentioning

confidence: 99%

“…The biologically potent 1,2,4-benzothiadiazine-1,1-dioxide ring is usually assembled through the reaction of o-aminoaryl-sulfonamides with either orthoesters [5] or acylating reagents. [6,7] The main disadvantage of this approach is a limited availability of o-aminosulfonamides, narrowing the chemical space for drug design. An alternative one-pot approach to the 1,2,4-benzothiadiazine-1,1-dioxide ring is based on the Michael addition of chlorosulfonyl isocyanate to aniline derivatives followed by the ring closure under Friedel-Crafts conditions.…”

Section: Introductionmentioning

confidence: 99%

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Facile Synthesis of 4H-1,2,4-Benzothiadiazine-1,1-dioxides

Cherepakha

Kovtunenko

Tolmachev

et al. 2011

Synthetic Communications

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o-Bromoarylsulfonylated amidines prepared either by acylation of amidine with o-bromoarylsulfonyl chloride or through the reaction of o-bromoarylsulfoamide with lactime ether underwent Cu(I)-catalyzed intramolecular cyclization to give 4H-1,2,4-benzothiadiazine-1,1-dioxides in good yield. By varying substituents on arylsulfonyl moieties, amidines, and lactime ethers, a small library of structurally diverse 4H-1,2,4-benzothiadiazine-1,1-dioxide derivatives was prepared.

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Section: Resultsmentioning

confidence: 96%

“…(%) for C 10 H 11 BrN 2 O 4 S 2 : C, 32.71; H, 3.02; Br,21.76;N,7.63. Found: C,32.52;H,3.09;Br,21.53;N,7.52. 8.60 (s,1 H,ArH).…”

Section: General Procedures For Preparation Of Sulfonylated Amidines (mentioning

confidence: 99%

“…(%) for C 10 H 10 Br 2 N 2 O 2 S: C,31.44;H,2.64;Br,41.38;N,7.33. Found: C,31.25;H,2.59;Br,41.72;N,7.28.…”

Section: General Procedures For Preparation Of Sulfonylated Amidines (mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Facile Synthesis of 4H-1,2,4-Benzothiadiazine-1,1-dioxides

Cherepakha

Kovtunenko

Tolmachev

et al. 2011

Synthetic Communications

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“…There have been numerous reports of the solid-phase syntheses of quinazoline-2,4-diones from resin-bound compounds with primary amines [6][7][8][9][10][11][12][13][14]. Construction of the quinazoline-2,4-dione skeleton on solid-support has been achieved either by urea bond formation followed by amide bond formation [6a,b], or vice versa [6c-e] (Fig.…”

Section: Solid-phase Synthesis Of Quinazoline-24-dionesmentioning

confidence: 99%

Solid-Phase Synthesis of Quinazoline-2,4-Diones and Their Analogues from Resin-Bound Compounds with Primary Amines

Makino¹

2006

MRMC

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Solid-phase organic synthesis of heterocyclic compounds on solid-support has been a focus of recent investigations because of the potential applicability of these compounds toward a variety of drug targets. Among the various heterocycles, we have been especially interested in quinazoline-2,4-diones because of the wide range of their bioactivities. Therefore, in this article we review methods for the solid-phase synthesis of quinazoline-2,4-diones and their analogues. Since all of these heterocycles can be speedily derivatized from resin-bound primary amines, incorporating the amines at the 3N-position of quinazoline-2,4-diones or corresponding positions of its analogues, it becomes possible to efficiently compare the bioactivities of these quinazoline-2,4-diones and their analogues. Various methods of solid-phase synthesis described herein should be practical and useful tools for the medicinal chemist in supporting drug discovery initiatives.

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A Noncatalytic Approach to Hetaryl‐Annulated 1,2,4‐Thiadiazine‐1,1‐dioxides

Cherepakha

Kovtunenko

Tolmachev

et al. 2013

Journal of Heterocyclic Chem

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A set of synthetic procedures was developed to yield functionalized pyrido‐, pyrimido‐, and thiazo‐annulated thiadiazine‐1,1‐dioxides on a preparative scale. In all cases the thiadiazine‐1,1‐dioxide ring closure was carried out through a reaction of hetaryl‐sulfonyl chlorides with amidines under mild noncatalytic conditions. In the case of 2‐chloropyridine‐3‐sulfonyl chloride derivatives and 2,4‐dichlorothiazole‐5‐sulfonyl chloride open‐chain sulfonylated amidine intermediates were isolated and then subjected to the cyclization step. The reaction with 2,4‐dichloropyrimidine‐5‐sulfonyl chloride gave rise to the corresponding thiadiazine‐1,1‐dioxides in one‐pot. Similarly, a reaction of 2‐chloropyridine‐3‐sulfonamide with lactime ethers proceeded in one‐pot readily giving the corresponding thiadiazine‐1,1‐dioxides. Remaining chlorine atoms on the prepared hetaryl‐annulated benzothiadiazine‐1,1‐dioxides readily undergo aromatic nucleophilic displacement reactions serving thus as additional variation points for the design of biologically potent compounds.

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Solid-phase synthesis of 2-substituted-3-(substituted sulfanyl)-1,2,4-benzothiadiazine 1,1-dioxide library

Cited by 14 publications

References 20 publications

Facile Synthesis of 4H-1,2,4-Benzothiadiazine-1,1-dioxides

Facile Synthesis of 4H-1,2,4-Benzothiadiazine-1,1-dioxides

Solid-Phase Synthesis of Quinazoline-2,4-Diones and Their Analogues from Resin-Bound Compounds with Primary Amines

A Noncatalytic Approach to Hetaryl‐Annulated 1,2,4‐Thiadiazine‐1,1‐dioxides

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