A PTC ASSISTED THIONATION: SYNTHESIS OF 2H-1,4- BENZOXAZINE-3(4H)-THIONES &amp; 2h-1,4-BENZOTHIAZINE- 3(4H)-THIONES

Introduction 3419 2. Reactions of P 4 S 10 3421 2.1. Ketones 3421 2.2. Thionoesters, Dithioesters, Thionolactones, Dithiolactones, Thiolactones, and Dithiolethiones 3426 2.3. Amides and Lactams 3435 2.4. Imides 3448 2.5. Thiophenes 3451 2.6. Thiazolines, Thiazoles, and Thiazines 3454 2.7. Dithiazoles 3456 2.8. Thiadiazoles 3456 2.9. Imidazolines and Pyrimidines 3456 2.10. Alcohols 3458 2.11. PdO to PdS 3461 2.12. Reduction 3462 2.13. Nucleotides, Purines, and Pyrimidines 3463 2.14. Miscellaneous 3467 2.15. P 4 S 10 vs Lawesson's Reagent (LR) 3473 3. Conclusion 3473 4. Acknowledgments 3473 5. References 3473

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Direct Formation of Ring-Fused 1,3-Thiazine-2,4-dithiones from Aromatic o-Amino Carboxylic Acids: Observation of a Carbon Disulfide Mediated Thionation

Ottersbach

Elsinghorst

Häcker

et al. 2010

Org. Lett.

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A facile synthesis of 2H-3,1-benzothiazine-2,4(1H)-dithiones (trithioisatoic anhydrides) or 2H-naphtho[2,3-d][1,3]thiazine-2,4(1H)-dithione solely from anthranilic acids or 3-amino-2-naphthoic acid and carbon disulfide, performed at room temperature in 1,4-dioxane in the presence of Et(3)N, is reported. Corresponding 2-alkylsulfanyl derivatives were obtained in one-pot reactions under the same conditions after addition of alkyl halides. The mechanism of the thiazine cyclization was investigated using (13)C-labeled carbon disulfide to reveal that carbon disulfide was incorporated into the heterocycle and additionally acted as a thionation reagent.

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A PTC ASSISTED THIONATION: SYNTHESIS OF 2H-1,4- BENZOXAZINE-3(4H)-THIONES & 2h-1,4-BENZOTHIAZINE- 3(4H)-THIONES

Cited by 3 publications

References 5 publications

ChemInform Abstract: A PTC Assisted Thionation: Synthesis of 2H‐1,4‐Benzoxazine‐3(4H)‐thiones and 2H‐1,4‐Benzothiazine‐3(4H)‐thiones.

ChemInform Abstract: A PTC Assisted Thionation: Synthesis of 2H‐1,4‐Benzoxazine‐3(4H)‐thiones and 2H‐1,4‐Benzothiazine‐3(4H)‐thiones.

A Berzelius Reagent, Phosphorus Decasulfide (P₄S₁₀), in Organic Syntheses

Direct Formation of Ring-Fused 1,3-Thiazine-2,4-dithiones from Aromatic o-Amino Carboxylic Acids: Observation of a Carbon Disulfide Mediated Thionation

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A PTC ASSISTED THIONATION: SYNTHESIS OF 2H-1,4- BENZOXAZINE-3(4H)-THIONES & 2h-1,4-BENZOTHIAZINE- 3(4H)-THIONES

Cited by 3 publications

References 5 publications

ChemInform Abstract: A PTC Assisted Thionation: Synthesis of 2H‐1,4‐Benzoxazine‐3(4H)‐thiones and 2H‐1,4‐Benzothiazine‐3(4H)‐thiones.

ChemInform Abstract: A PTC Assisted Thionation: Synthesis of 2H‐1,4‐Benzoxazine‐3(4H)‐thiones and 2H‐1,4‐Benzothiazine‐3(4H)‐thiones.

A Berzelius Reagent, Phosphorus Decasulfide (P4S10), in Organic Syntheses

Direct Formation of Ring-Fused 1,3-Thiazine-2,4-dithiones from Aromatic o-Amino Carboxylic Acids: Observation of a Carbon Disulfide Mediated Thionation

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Product

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A Berzelius Reagent, Phosphorus Decasulfide (P₄S₁₀), in Organic Syntheses