Synthesis of imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazines via a base-induced rearrangement of functionalized imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazines

• Dmitry B. Vinogradov,
• Alexei N. Izmest’ev,
• Angelina N. Kravchenko,
• Yuri A. Strelenko and
• Galina A. Gazieva

Beilstein J. Org. Chem. 2023, 19, 1047–1054, doi:10.3762/bjoc.19.80

• rearrangement; 1,3-thiazines; thiazolidine-4-ones; Introduction Nitrogen- and sulfur-containing heterocyclic compounds are widely represented in nature and used for the synthesis of biologically active substances. Among the 1,3-thiazine derivatives, promising compounds as antimicrobial and antiviral drugs

Microwave-assisted synthesis of 2-substituted 4,5,6,7-tetrahydro-1,3-thiazepines from 4-aminobutanol

• María C. Mollo,
• Natalia B. Kilimciler,
• Juan A. Bisceglia and
• Liliana R. Orelli

Beilstein J. Org. Chem. 2020, 16, 32–38, doi:10.3762/bjoc.16.5

• as building blocks in drug discovery, and as ligands in metal-catalyzed reactions [11][12][13][14][15][16]. Their six-membered homologues (5,6-dihydro-4H-1,3-thiazines) are also compounds of broad interest [17], due to their bioactivities [18][19] and as valuable synthetic intermediates [20][21][22

N-Propargylamines: versatile building blocks in the construction of thiazole cores

• S. Arshadi,
• E. Vessally,
• L. Edjlali,
• R. Hosseinzadeh-Khanmiri and
• E. Ghorbani-Kalhor

Beilstein J. Org. Chem. 2017, 13, 625–638, doi:10.3762/bjoc.13.61

• mixture of 4H-1,3-thiazines 56 and 4,5-dihydrothiazoles 57. The mechanistic course of this reaction sequence is shown in Scheme 17 and involves the initial formation of the charge-transfer complex A between the iodonium ion and the triple bond. The 5-exo-dig cyclization of this intermediate gives rise to

• 4,5-dihydrothiazoles and the competing 6-endo-dig ring-closing process affords 4H-1,3-thiazines after conversion of the charge-transfer complex into the ring-opened iodovinyl B or bridged iodirenium C ions; (2) bromine-mediated cyclizations of both electron-poor and electron-rich N-propargylthioureas

• internal N-propargylamines 55 under the same reaction conditions gave a mixture of 57 and 56; (4) arylideneoxonium ion-mediated cyclization of internal N-propargylamines 55 afforded exclusively the corresponding 4H-1,3-thiazines 56 in good yields. However, terminal N-propargylamines failed to participate

Secondary amine-initiated three-component synthesis of 3,4-dihydropyrimidinones and thiones involving alkynes, aldehydes and thiourea/urea

• Jie-Ping Wan,
• Yunfang Lin,
• Kaikai Hu and
• Yunyun Liu

Beilstein J. Org. Chem. 2014, 10, 287–292, doi:10.3762/bjoc.10.25

• solid. Some DHPMs-based lead compounds. Regioselective 1,3-thiazines and DHPMs via aldehydes, ureas/thioureas and alkynes. Synthesis of enamino ester intermediate and its transformation to DHPM. Proposed reaction mechanism. Optimization of reaction conditionsa. Multicomponent synthesis of different

New simple synthesis of ring-fused 4-alkyl-4H-3,1-benzothiazine-2-thiones: Direct formation from carbon disulfide and (E)-3-(2-aminoaryl)acrylates or (E)-3-(2-aminoaryl)acrylonitriles

• Qiuping Ding,
• Yuqing Lin,
• Guangni Ding,
• Fumin Liao,
• Xiaoyan Sang and
• Yi-Yuan Peng

Beilstein J. Org. Chem. 2013, 9, 460–466, doi:10.3762/bjoc.9.49

• of novel natural-product-like compounds [18][19][20][21][22], we recently reported the practical synthesis of 2-mercapto-4-benzylidene-4H-benzo[d][1,3]thiazines starting from 2-alkynylbenzenamines with CS2, and further transformations to highly functionalized 4-benzylidene-4H-benzo[d][1,3]thiazines