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Journal articles on the topic '5-thiadiazine dioxides'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

Innes, Dylan, Michael V. Perkins, Andris J. Liepa, and Craig L. Francis. "N,N-Dialkyl-N′-Chlorosulfonyl Chloroformamidines in Heterocyclic Synthesis. Part XIV. Synthesis and Reactivity of the New Benzo[4,5]imidazo[1,2-b][1,2,6]thiadiazine Ring System." Australian Journal of Chemistry 71, no. 1 (2018): 58. http://dx.doi.org/10.1071/ch17255.

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N,N-Dialkyl-N′-chlorosulfonyl chloroformamidines 1 underwent regioselective reactions with the 1,3-NCC bis-nucleophilic 1H-benzimidazole-2-acetonitriles 4 and related compounds to produce benzo[4,5]imidazo[1,2-b][1,2,6]thiadiazine dioxides 6, 9, 12, and 14, representatives of a new ring system. Reaction of dichlorides 1 with trifluoroacetyl derivative 16 afforded benzo[4,5]imidazo[1,2-c]pyrimidines 19 and 20. An N-acyl and some N-alkyl derivatives of benzimidazo-thiadiazines 6 were prepared to demonstrate the potential of this new ring system as a novel scaffold for synthetic and medicinal che

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2

Di Santo, R., R. Costi, M. Artico, et al. "1,2,5-Benzothiadiazepine and Pyrrolo[2,1-d]-[1,2,5]Benzothiadiazepine Derivatives with Specific Anti-Human Immunodeficiency Virus Type 1 Activity." Antiviral Chemistry and Chemotherapy 9, no. 2 (1998): 127–37. http://dx.doi.org/10.1177/095632029800900204.

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We synthesized and tested as novel inhibitors of human immunodeficiency virus type 1 (HIV-1) bi- and tricyclic thiadiazine ring homologues of 7-chloro-2-ethyl-2 H-1,2,4-benzothiadiazin-3-(4 H)-one 1,1-dioxide, which is a compound endowed with anti-HIV-1 activity at low micromolar concentrations. Benzothiadiazepine derivatives were obtained by alkylation of 8-chloro-2,3-dihydro-3-methyl-1,2,5-benzothiadiazepin-4(5 H)-one 1,1-dioxide, which was obtained by intramolecular cyclization of 2-(2-amino-5-chloro-benzenesulphonamido) propanoic acid. Pyrrolobenzothiadiazepines were synthesized from N-sub

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3

LEE, C. H., Y. H. LEE, W. S. CHOI, and B. Y. CHUNG. "ChemInform Abstract: Synthesis of 4-Carbethoxy-5-aryl-5,6-dihydro-2H-1,2,6-thiadiazine 1,1- Dioxides." ChemInform 24, no. 16 (2010): no. http://dx.doi.org/10.1002/chin.199316216.

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4

Innes, Dylan, Michael V. Perkins, Andris J. Liepa, and Craig L. Francis. "N,N-Dialkyl-N′-Chlorosulfonyl Chloroformamidines in Heterocyclic Synthesis. Part XV. Some Unexpected Reactions with Anilines." Australian Journal of Chemistry 71, no. 8 (2018): 610. http://dx.doi.org/10.1071/ch18252.

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N,N-Dimethyl-N′-chlorosulfonyl chloroformamidine 1a underwent reactions with various anilines. In addition to the benzo[e][1,2,4]thiadiazine dioxides 8, from 1,3-NCC bis-nucleophilic substitution and bis-anilino adducts 9, some unexpected products were formed, particularly when sterically hindered or electron-poor anilines were used. In these cases, products such as the [1,3,2,4,6]dithiatriazine 1,1,3,3-tetraoxides 17 and, on occasion, N,N,5-trimethyl-4-(arylimino)-4,5-dihydro-[1,3,5]triazin-2-amines 14 were produced in significant yields. Reaction of dichloride 1a with 3-bromoaniline afforded

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5

Susanta, K. Borthakur, Boruah Paran, and N. Goswami Birendra. "[4+2] Cycloaddition reaction: Synthesis and antifungal activities of 2-substituted 1,2,4-triazolo[3,2-c][1,3,5]thiadiazine-3,3-dioxides." Journal of Indian Chemical Society Vol. 90, Jul 2013 (2013): 1005–8. https://doi.org/10.5281/zenodo.5774794.

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Department of Chemistry, Arya Vidyapeeth College, P.O. Gopinath Nagar, Guwahati-781 016, Assam, India <em>E-mail</em> : skbthakur@yahoo.co.in Medicinal Aromatic and Economic Plant Division, Formerly of Synthetic Organic Chemistry Division, North East Institute of Science and Technology, Jorhat-785 006, Assam, India <em>Manuscript received online 06 August 2012, revised 09 August 2012, accepted 16 August 2012</em> 3-Benzylidineamino-1,2,4-triazole undergoes [4+2] cycloaddition reaction with sulfene resulting in good yield of [1,2,4]-triazolo[3,2-<em>c</em>][1,3,5]-thiadiazine-3,3-dioxide deriva

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6

Goya, Pilar, and Ana Martinez. "N-Glucosyl-5-amino-4-carbamoyl- and 4-Ethoxycarbonylimidazoles as Potential Precursors of 4-Oxoimdazo[4,5-c]-1,2,6-thiadiazine 2,2-Dioxides." HETEROCYCLES 24, no. 12 (1986): 3451. http://dx.doi.org/10.3987/r-1986-12-3451.

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7

Ochoa, Carmen, Angela Herrero, Juan Antonio P�z, Mart地 Mart地ez-Ripoll, Concepci溶 Foces-Foces, and F四ix Hernadez Cano. "A New Route for the Synthesis of 6-Substitutes Imidazo[4-5,c]-1,2,6-thiadiazine 2,2-Dioxides: Nmr Study and Crystal Structure of a Complex with Dimethylformamide." HETEROCYCLES 26, no. 12 (1987): 3123. http://dx.doi.org/10.3987/r-1987-12-3123.

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8

Gong, Tang, Liu та Liu. "Synthesis and Evaluation of Novel 2H-Benzo[e]-[1,2,4]thiadiazine 1,1-Dioxide Derivatives as PI3Kδ Inhibitors". Molecules 24, № 23 (2019): 4299. http://dx.doi.org/10.3390/molecules24234299.

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In previous work, we applied the rotation-limiting strategy and introduced a substituent at the 3-position of the pyrazolo [3,4-d]pyrimidin-4-amine as the affinity element to interact with the deeper hydrophobic pocket, discovered a series of novel quinazolinones as potent PI3Kδ inhibitors. Among them, the indole derivative 3 is one of the most selective PI3Kδ inhibitors and the 3,4-dimethoxyphenyl derivative 4 is a potent and selective dual PI3Kδ/γ inhibitor. In this study, we replaced the carbonyl group in the quinazolinone core with a sulfonyl group, designed a series of novel 2H-benzo[e][1

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9

Clerici, Francesca, Franco Galletti, Donato Pocar, and Pietro Roversi. "Isothiazoles. Part VI. Cycloaddition of azides to isothiazole dioxides: Synthesis of thiadiazabicyclo[3.1.0]hexene derivatives and their thermal rearrangement to thiazete dioxides, 1,2,6-thiadiazine dioxides and pyrazoles." Tetrahedron 52, no. 20 (1996): 7183–200. http://dx.doi.org/10.1016/0040-4020(96)00336-5.

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10

Gobis, Katarzyna, Henryk Foks, Jarosłw Sławiński, Ewa Augustynowicz-Kopeć, and Agnieszka Napiórkowska. "Synthesis and biological activity of novel 3-heteroaryl-2H-pyrido[4,3-e][1,2,4]thiadiazine and 3-heteroaryl-2H-benzo[e][1,2,4]thiadiazine 1,1-dioxides." Monatshefte für Chemie - Chemical Monthly 144, no. 8 (2013): 1197–203. http://dx.doi.org/10.1007/s00706-013-0988-5.

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11

Brouant, Pierre, Jacques Barbe, Pilar Goya, and Carmen Ochoa. "Étude structurale de l'amino-5 dibenzyl-4,4 one-3 2H-thiadiazine-1,2,6 dioxyde-1,1." Canadian Journal of Chemistry 66, no. 10 (1988): 2477–82. http://dx.doi.org/10.1139/v88-389.

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5-Amino-4,4-dibenzyl-3-one-2H-1,2,6-thiadiazine-1,1-dioxide was structurally characterized in the solid state by X-ray diffraction. The structure shows that the title compound exists in the solid in a sheet-packed form and as the amino tautomer. The unconjugated heterocyclic ring, which in the structures of related compounds is usually folded, is planar in the present structure. 1H nuclear magnetic resonance and dipole moment data indicate that the title compound has the same structure in the solid state and in solution.

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12

Chatla, Aruna Jyothi, Nagaraju Dharavath, Praveen Mamidala, Poorna Chandar Gugulothu, and Jayaprakash Rao Yerrabelly. "Synthesis, Anticancer and EGFR Inhibitory Activity of Novel [1,2,4]Triazolo[3,4-b][1,3,4]thiadiazine-isoxazoles." Asian Journal of Chemistry 37, no. 5 (2025): 1237–45. https://doi.org/10.14233/ajchem.2025.33420.

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A novel approach was utilized for the synthesis of new [1,2,4]triazolo[3,4-b] [1,3,4]thiadiazine containing isoxazoles (6a-o) from 3-ethynyl-6-(4-fluorophenyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine-8,8-dioxide (4) in combination with freshly prepared substituted nitrile oxides (5) using Cu(I)-catalyzed [3+2] cycloaddition method. The in vitro cancer activity of the synthesized compounds was carried out against two lung cancer cell lines, A-549 and H1299. Among the compounds tested, 6h, 6k and 6l exhibited significantly stronger anticancer activity compared to standard drug erlotinib, wit

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13

BREINING, T., A. R. CIMPOIA, T. S. MANSOUR, N. CAMMACK, P. HOPEWELL, and C. ASHMAN. "ChemInform Abstract: 1′,2′,6′-Thiadiazine 1′,1′-Dioxide and Imidazo (4′,5′-c) (1′,2′,6′)- Thiadiazine 2′,2′-Dioxide 1,3-Oxathiolane Nucleoside Analogues: Synthesis and Anti-HIV-1 Activity." ChemInform 26, no. 26 (2010): no. http://dx.doi.org/10.1002/chin.199526251.

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14

Norman, Rebecca E., Michael V. Perkins, Andris J. Liepa, and Craig L. Francis. "N,N-Dialkyl-N′-Chlorosulfonyl Chloroformamidines in Heterocyclic Synthesis. Part XIII. Cleavage and Rearrangement Reactions of Pyrazolo[1,5-b][1,2,4,6]thiatriazine 1,1-Dioxides." Australian Journal of Chemistry 69, no. 1 (2016): 61. http://dx.doi.org/10.1071/ch15445.

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Treatment of pyrazolo[1,5-b][1,2,4,6]thiatriazines 1 with the Vilsmeier–Haack reagent afforded pyrazolo[1,5-a][1,3,5]triazines 5. Reaction of compounds 1 with trifluoroacetic anhydride, dimethyl sulfoxide, and triethylamine afforded 5-dimethylsulfanylidene derivatives 8. The guanidino-pyrazole-sulfonic acid 9 was produced from treatment of compounds 1 with trifluoroacetic acid under anhydrous conditions. Similar treatment in the presence of water afforded the desulfonated pyrazolo-guanidine 6. Reactions of 6 with one-carbon electrophiles provided various 4-substituted pyrazolo[1,5-a][1,3,5]tri

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15

Vicentini, C. B., A. C. Veronese, T. Poli, M. Guarneri, P. Giori, and V. Ferretti. "A new fused heterocyclic system: 6H-pyrazolo[3, 4-c][1, 2, 5]thiadiazine 2, 2-dioxide." Journal of Heterocyclic Chemistry 26, no. 3 (1989): 797–803. http://dx.doi.org/10.1002/jhet.5570260354.

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16

S. Mansour, Tarek, Tibor Breining, Alex R. Cimpoia, Nick Cammack, Philippa Hopewell, and Claire Ashman. "1',2',6'-Thiadiazine 1',1'-Dioxide and Imidazo [4',5'-c][1',2',6']thiadiazine 2',2'-Dioxode 1,3-Oxathiolane Nucleoside Analogues: Synthesis and Anti-HIV-1 Activity." HETEROCYCLES 41, no. 1 (1995): 87. http://dx.doi.org/10.3987/com-94-6887.

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17

Arthur, Amy J., Donald S. Karanewsky, Mike Luksic, Geoff Goodfellow, and Jon Daniels. "Toxicological evaluation of two flavors with modifying properties: 3-((4-amino-2,2-dioxido-1H-benzo[c][1,2,6]thiadiazin-5-yl)oxy)-2,2-dimethyl-N-propylpropanamide and (S)-1-(3-(((4-amino-2,2-dioxido-1H-benzo[c][1,2,6]thiadiazin-5-yl)oxy)methyl)piperidin-1-yl)-3-methylbutan-1-one." Food and Chemical Toxicology 76 (February 2015): 33–45. http://dx.doi.org/10.1016/j.fct.2014.11.018.

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18

Goya, P., A. Martínez, and C. Ochoa. "Synthesis of 2S-Dioxo Isosteres of Purine and Pyrimidine Nucleosides IV. Selective Glycosylation of 4-Amino-5H-Imidazo [4, 5-c]-1, 2, 6-Thiadiazine 2, 2-Dioxide." Nucleosides, Nucleotides and Nucleic Acids 6, no. 3 (1987): 631–42. http://dx.doi.org/10.1080/07328318708069992.

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19

Citti, Cinzia, Umberto M. Battisti, Giuseppe Cannazza та ін. "7-Chloro-5-(furan-3-yl)-3-methyl-4H-benzo[e][1,2,4]thiadiazine 1,1-Dioxide as Positive Allosteric Modulator of α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid (AMPA) Receptor. The End of the Unsaturated-Inactive Paradigm?" ACS Chemical Neuroscience 7, № 2 (2015): 149–60. http://dx.doi.org/10.1021/acschemneuro.5b00257.

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20

Karanewsky, Donald S., Guy Servant, Hanghui Liu, et al. "Toxicological evaluation of the flavour ingredient N -(1-((4-amino-2,2-dioxido-1 H -benzo[ c ][1,2,6]thiadiazin-5-yl)oxy)-2-methylpropan-2-yl)-2,6-dimethylisonicotinamide (S2218)." Toxicology Reports 4 (2017): 507–20. http://dx.doi.org/10.1016/j.toxrep.2017.09.004.

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21

GOYA, P., and A. MARTINEZ. "ChemInform Abstract: N-Glucosyl-5-amino-4-carbamoyl- and 4-Ethoxycarbonylimidazoles as Potential Precursors of 4-Oxoimidazo(4,5-c)-1,2,6-thiadiazine 2,2-Dioxides." ChemInform 18, no. 21 (1987). http://dx.doi.org/10.1002/chin.198721192.

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22

Shalimov, Oleksandr, Mykola Kolotylo, Dmytro Otsaliuk, Svitlana Shishkina, Oksana Muzychka, and Petro Onys'ko. "Efficient Synthesis of Fused Heterocycles Incorporating Pyrazole/Thiadiazine or Pyrazole/Thiadiazepine Fragments Using N‐Chlorosulfonyltrihaloacetimidoyl Chlorides." ChemistrySelect 8, no. 43 (2023). http://dx.doi.org/10.1002/slct.202302929.

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AbstractA novel simple and effective method has been developed for constructing pyrazolothiadiazine and pyrazolothiadiazepine fused heterocycles incorporating an endocyclic sulfonamide fragment. The cyclocondensation of readily available N‐(chlorosulfonyl)imidoyl chlorides, RC(Cl)=NSO2Cl (R=CCl3, CF2Br), with N‐methyl‐substituted 4‐ or 5‐aminopyrazoles results in the formation of isomeric pyrazolothiadiazine‐S,S‐dioxides. Additionally, when 5‐ or 3‐aminoalkyl‐substituted pyrazoles are employed, they serve as 1,4‐N−C−C−C binucleophiles, leading to the synthesis of novel pyrazolothiadiazepine he

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23

Goffin, Eric, Pierre Fraikin, Dayana Abboud, et al. "New Insights In The Development of Positive Allosteric Modulators of A-Amino-3-Hydroxy-5-Methyl-4-Isoxazolepropionic Acid (AMPA) Receptors Belonging To 3,4-Dihydro-2H-1,2,4-Benzothiadiazine 1,1-Dioxides: Introduction of (Mono/Difluoro)Methyl Groups At The 2-Position of the Thiadiazine Ring." SSRN Electronic Journal, 2023. http://dx.doi.org/10.2139/ssrn.4329581.

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24

Goffin, Eric, Pierre Fraikin, Dayana Abboud та ін. "New insights in the development of positive allosteric modulators of α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) receptors belonging to 3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxides: Introduction of (mono/difluoro)methyl groups at the 2-position of the thiadiazine ring". European Journal of Medicinal Chemistry, лютий 2023, 115221. http://dx.doi.org/10.1016/j.ejmech.2023.115221.

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25

Mosesso, Pasquale. "Scientific Opinion of Flavouring Group Evaluation 406." February 1, 2018. https://doi.org/10.2903/j.efsa.2018.5120.

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The Panel on Food Contact Materials, Enzymes, Flavourings and Processing Aids (CEF) of EFSA was requested to deliver a scientific opinion on the safety of the use of the substance (S)-1-(3-(((4-amino2,2-dioxido-1H-benzo[c][1,2,6]thiadiazin-5-yl)oxy)methyl)piperidin-1-yl)-3-methylbutan-1-one [FL-no: 16.129], as a flavouring substance. The substance is intended to be used in the form of its sodium salt as a flavour modifier in beverages. The Panel concluded that [FL-no: 16.129] would not raise a concern with respect to genotoxicity under conditions where it remains stable and does not undergo ph

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26

Silano, Vittorio, Claudia Bolognesi, Laurence Castle, et al. "Scientific Opinion of Flavouring Group Evaluation 406 (FGE.406): (S)‐1‐(3‐(((4‐amino‐2,2‐dioxido‐1H‐benzo[c][1,2,6]thiadiazin‐5‐yl)oxy)methyl)piperidin‐1‐yl)‐3‐methylbutan‐1‐one." EFSA Journal 16, no. 2 (2018). http://dx.doi.org/10.2903/j.efsa.2018.5120.

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