Synthesis Of Thiopyrano Research Articles

Trans-Aconitic acid-based hetero-Diels-Alder reaction in the synthesis of thiopyrano[2,3-d][1,3]thiazole derivatives

The hetero-Diels-Alder reaction of 5-arylideneisorhodanines with trans-aconitic acid proceeds as a regio- and diastereoselective process with spontaneous decarboxylation of the [4+2]-adduct to furnish thiopyrano[2,3-d][1,3]thiazole (2) and chromeno[4′,3′:4,5]thiopyrano[2,3-d]thiazole (3) derivatives analogously to the use of itaconic acid as a dienophile. Conversely, the one-pot, three-component reaction of 5-arylideneisorhodanines, trans-aconitic acid and anilines proceeded without decarboxylation, leading to novel rel-(5′R,6′R,7′R)-5′-carboxy-7′-aryl-1-aryl-3′,7′-dihydro-2H,2′H,5H-spiro[pyrrolidin-3,6′-thiopyrano[2,3-d]thiazol]-2,2′,5-triones 4. Interestingly, the use of trans-aconitic acid trimethyl ester led to the opposite regioselectivity, yielding rel-(5R,6S,7S)-5-methyloxycarbonylmethyl-2-oxo-7-aryl-3,5,6,7-tetrahydro-2H-thiopyrano[2,3-d]thiazol-5,6-dicarboxylates 5. Selected compounds were examined for trypanocide activity against the bloodstream forms of Trypanosoma brucei where compound 4e showed the highest activity (IC50=6.74μM).

ChemInform Abstract: An Efficient One‐Pot Regioselective Approach Towards the Synthesis of Thiopyrano[2,3‐d]thiazole‐2‐thiones Catalyzed by Basic Ionic Liquid under Microwave Irradiation.

AbstractA green method for preparation of the title thiopyran derivatives by cyclocondensation of (thioxo)thiazolidinone, benzaldehydes, and β‐oxodithioesters using ionic liquid as catalyst and solvent is developed.

Crotonic, cynnamic, and propiolic acids motifs in the synthesis of thiopyrano[2,3-d][1,3]thiazoles via hetero-Diels–Alder reaction and related tandem processes

Various novel thiopyrano[2,3-d][1,3]thiazol-2-one-6-carboxylic acids derivatives were synthesized in 54–86% yields via hetero-Diels–Alder reactions and related acylation-based tandem processes of 5-arylidene-4-thioxo-2-thiazolidinones with crotonic, propiolic, and cynnamic acids derivatives. Stereo- and regioselectivity of cycloaddition were investigated.

ChemInform Abstract: Iodine‐Catalyzed Synthesis of Thiopyrano[3,4‐c]quinoline Derivatives via Imino‐Diels—Alder Reaction.

AbstractThe title compounds (IV) and (VI) are efficiently obtained via a mild iodine‐catalyzed imino‐Diels—Alder reaction of various aromatic aldehydes (II), 5‐amino‐1H‐indazole (I) or 2‐aminoanthracene (V), and tetrahydrothiopyran‐4‐one (III).

ChemInform Abstract: Rapid, Clean and Efficient One‐Pot Synthesis of Thiopyrano[2,3‐b]quinolines via Domino Michael Addition/Cyclization Reactions.

AbstractThe sequence proceeds smoothly and does not require dry solvent or inert atmosphere.

A convenient method for the synthesis of thiopyrano[4,3-c]quinoline, a new heterocyclic system

A convenient method for the synthesis of thiopyrano[4,3-c]quinoline, a new heterocyclic system

ChemInform Abstract: Synthesis of Thiopyrano(2,3‐d)pyrimidines and Thieno(2,3‐d)pyrimidines.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Activated Nitriles in Heterocyclic Synthesis: Novel Synthesis of Thiopyrano[2,3-d]thiazoles

Activated Nitriles in Heterocyclic Synthesis: Novel Synthesis of Thiopyrano[2,3-d]thiazoles

ChemInform Abstract: REACTIONS WITH THIOHYDANTOINS: A NOVEL SYNTHESIS OF THIOPYRANO(2,3‐D)IMIDAZOLES

Chemischer InformationsdienstVolume 13, Issue 40 Heterocyclic Compounds ChemInform Abstract: REACTIONS WITH THIOHYDANTOINS: A NOVEL SYNTHESIS OF THIOPYRANO(2,3-D)IMIDAZOLES H. A. DABOUN, H. A. DABOUNSearch for more papers by this authorM. A. ABDEL AZIZ, M. A. ABDEL AZIZSearch for more papers by this authorF. A. ABDEL AAL, F. A. ABDEL AALSearch for more papers by this author H. A. DABOUN, H. A. DABOUNSearch for more papers by this authorM. A. ABDEL AZIZ, M. A. ABDEL AZIZSearch for more papers by this authorF. A. ABDEL AAL, F. A. ABDEL AALSearch for more papers by this author First published: October 5, 1982 https://doi.org/10.1002/chin.198240190AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume13, Issue40October 5, 1982 RelatedInformation

Synthesis of thiopyrano[2,3‐d] pyrimidines and thieno[2,3‐d]pyrimidines

AbstractThe reaction of 4‐chloro‐5‐cyano‐2‐methylthiopyrimidine (I) with ethyl mercaptosuccinate (II) in refluxing ethanol containing sodium carbonate has afforded diethyl 3‐amino‐2‐(methyl‐thio)‐7H‐thiopyrano[2,3‐d]pyrimidine‐6,7‐dicarboxylate (IV). Displacement of the methylthio group in IV with hydrazine gave the corresponding hydrazino derivative which underwent Schiff base formation with benzaldehyde or 2,6‐dichlorobenzaldehyde. Treatment of IV in refluxing acetic anhydride afforded the corresponding diacetylated amino derivative. Partial saponification of IV with sodium hydroxide gave 5‐amino‐2‐(methylthio)‐7H‐thiopyrano‐[2,3‐d]pyrimidine 6,7‐dicarboxylic acid 6 ethyl ester (VIII). The reaction of 4‐amino‐6‐chloro‐5‐cyano‐2‐phenylpyrirnidine (XI) with II resulted in the formation of ethyl 4‐amino‐6‐(ethoxy‐carbonyl)‐5,6‐dihydro‐5‐amino‐2‐phenylthieno[2,3‐d]pyrimidine‐6‐acetate (XIII) which when subjected to hydrolysis gave ethyl 4,5‐diamino‐2‐phenylthieno[2,3‐d]pyrimidine‐6‐acetate isolated as the hydrochloride (XIV). Diazotization of IV with sodium nitrite in acetic acid unexpectedly afforded diethyl 5‐(acetyloxy)‐6,7‐dihydro‐6‐hydroxy‐2‐(methylthio)‐5H‐thio‐pyrano[2,3‐d]pyrimidine‐6,7‐diearboxylate (XV). Several structural ambiguities were resolved by ir and pmr spectra.

Synthesis of pyrazolone-derivatives. XXV. Synthesis of thiopyrano(3,4-c)pyrazoles (author's transl)

Synthesis of pyrazolone-derivatives. XXV. Synthesis of thiopyrano(3,4-c)pyrazoles (author's transl)