Reactions of o-aminothiophenol withαβ-unsaturated dicarbonyl systems. Facile synthesis of benzothiazines and benzothiazepines

Balasubramaniyan, V.; Balasubramaniyan, P.; Shaikh, Abid

doi:10.1016/s0040-4020(01)90560-5

Cited by 19 publications

(6 citation statements)

References 44 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A definitive study on structural details of the products of these conversions appears desirable. The present study is focussed on these aspects and will also extend our earlier observations on the role of electronic effects in Michael additions of heteroatom nucleophiles with maleic anhydride derivatives (Balasubramaniyan et al 1986(Balasubramaniyan et al , 1990.…”

Section: Introductionmentioning

confidence: 78%

Reactions of cyclic anhydrides. Part XXII. Direct synthesis of N-aryl-α-(2,3,4,5-tetrahydro-2-imino-4-oxo-1,3-thiazoIe-5-yl) acetamides

Balasubramaniyan¹,

Balasubramaniyan²,

Wani³

1991

Proc. Indian Acad. Sci. (Chem. Sci.)

Self Cite

View full text Add to dashboard Cite

react with thiourea in refluxing ethanol to yield the corresponding N-aryl ct-(2,3,4,5-tetrahydro-4-oxo-l,3-thiazole-5-yl) acetamides (6a-j_') in 72-85~o. The spectral and analytical data are consistent with the assigned structures for 6a-j. Under similar conditions, isomalemides 3(~-_b and 3d--f) furnish the corresponding 6a-_b and 6d-f in 76-86~. While maleanilic acid (4_.a) itself failed to react with thiourea, 4b--e_, 4i and 4j yielded a mixture of the corresponding 6___~e, 6i and 6j in 2-50~o and fumaranilic acids (7b--e_, 7i and 7j) in 50-80~. Methyl maleanilates 5~, 5d-f and ~ gave 6b,6d-_f and 6i in 78-85~. The reaction course of Raney nickel desulphurisation of 6a-_b, ~ 6f and mass spectral fragmentation of 6b support the assigned structures.

show abstract

Section: Introductionmentioning

confidence: 78%

Reactions of cyclic anhydrides. Part XXII. Direct synthesis of N-aryl-α-(2,3,4,5-tetrahydro-2-imino-4-oxo-1,3-thiazoIe-5-yl) acetamides

Balasubramaniyan¹,

Balasubramaniyan²,

Wani³

1991

Proc. Indian Acad. Sci. (Chem. Sci.)

Self Cite

View full text Add to dashboard Cite

show abstract

“…Indeed, 1,4‐benzothiazine ring 4 is of significant interest as it constitutes the skeleton of many synthetic drugs and bioactive compounds 22. This has led to the development of several synthetic methods, with some representative examples provided by the condensation between anilines and dicarbonyls or esters,23 between 2‐aminobenzenethiol and enoates,24 alkynes,25 or α‐halogenated carbonyl compounds,26 and moreover by the annulation of benzyl arylimines 27. Similarly, 1,2,3,4‐tetrahydroquinoxaline ( 5 ) and its derivatives are useful organic intermediates for pharmaceutical28 and many other applications.…”

Section: Resultsmentioning

confidence: 99%

Selective N‐Alkylation of Arylamines with Alkyl Chloride in Ionic Liquids: Scope and Applications

et al. 2012

View full text Add to dashboard Cite

An efficient N-selective alkylation of primary aromatic\ud amines in molten quaternary ammonium salts, as the solvent,\ud under relatively mild and base-free conditions is presented.\ud On the basis of the Kamlet–Taft parameters and the nucleophilicity\ud of the IL (ionic liquid) anions, the influence of the ionic liquid was evaluated. This protocol was validated on a\ud larger multigram scale and with the syntheses of bioactive\ud heterocycles (e.g., 1,4-benzothiazine and quinoxalines) and\ud new efficient MALDI matrixes

show abstract

“…It was reported that the nucleophilic attachment of aminouracil to N-substituted maleinimides may lead to physiologically active compounds probably possessing antitumor, anticonvulsive, or antimicrobial properties [8][9][10].…”

Section: IVmentioning

confidence: 99%

Synthesis of new substituted uracils and pyrimidines

1999

View full text Add to dashboard Cite

show abstract

Reactions of o-aminothiophenol withαβ-unsaturated dicarbonyl systems. Facile synthesis of benzothiazines and benzothiazepines

Cited by 19 publications

References 44 publications

Reactions of cyclic anhydrides. Part XXII. Direct synthesis of N-aryl-α-(2,3,4,5-tetrahydro-2-imino-4-oxo-1,3-thiazoIe-5-yl) acetamides

Reactions of cyclic anhydrides. Part XXII. Direct synthesis of N-aryl-α-(2,3,4,5-tetrahydro-2-imino-4-oxo-1,3-thiazoIe-5-yl) acetamides

Selective N‐Alkylation of Arylamines with Alkyl Chloride in Ionic Liquids: Scope and Applications

Synthesis of new substituted uracils and pyrimidines

Contact Info

Product

Resources

About