Reactions of acryl thioamides with iminoiodinanes as a one-step synthesis of N-sulfonyl-2,3-dihydro-1,2-thiazoles

• Vladimir G. Ilkin,
• Pavel S. Silaichev,
• Valeriy O. Filimonov,
• Tetyana V. Beryozkina,
• Margarita D. Likhacheva,
• Pavel A. Slepukhin,
• Wim Dehaen and
• Vasiliy A. Bakulev

Beilstein J. Org. Chem. 2025, 21, 1397–1403, doi:10.3762/bjoc.21.104

• iminoiodinanes. A library of 31 examples of tetrasubstituted 1,2-thiazoles was thus synthesized in high yields. The effectiveness of the synthesis method for these poorly studied 1,2-thiazoles was confirmed by scaling the reaction using gram amounts of the starting thioamide. Keywords: iminoiodinanes; sulfonyl

• groups; synthesis; 1,2-thiazolines; thioamides; Introduction 1,2-Thiazoles (isothiazoles) exhibit a wide range of biological activity (Figure 1): antipoliovirus [1], anticancer [2][3][4][5][6][7], against Parkinson's disease [8], and diabetes [9][10][11], and are also used as microbiocides [12][13

Quinoxaline derivatives as attractive electron-transporting materials

• Zeeshan Abid,
• Liaqat Ali,
• Sughra Gulzar,
• Faiza Wahad,
• Raja Shahid Ashraf and
• Christian B. Nielsen

Beilstein J. Org. Chem. 2023, 19, 1694–1712, doi:10.3762/bjoc.19.124

• the earlier [54]. Recently, Ding et al. prepared a novel air-stable n-type benzothiophene endcapped azaarene (BTPQ) and its sulfonated derivative (BSPQ). By introducing nitrogen atoms and sulfonyl groups, the researchers modulated the molecular energy levels and achieved the energy level requirements

Transition-metal-catalyzed domino reactions of strained bicyclic alkenes

• Austin Pounder,
• Eric Neufeld,
• Peter Myler and
• William Tam

Beilstein J. Org. Chem. 2023, 19, 487–540, doi:10.3762/bjoc.19.38

• naphthylation of oxabenzonorbornadienes 30 with N-sulfonyl 2-aminobenzaldehydes 172 (Scheme 30) [76]. This reaction was amenable to a variety of EDG, EWG, as well as a broad scope of sulfonyl groups. Surprisingly, this reaction also proceeded smoothly with nitro substituents on the benzene ring which are

Substituent effect on TADF properties of 2-modified 4,6-bis(3,6-di-tert-butyl-9-carbazolyl)-5-methylpyrimidines

• Irina Fiodorova,
• Tomas Serevičius,
• Rokas Skaisgiris,
• Saulius Juršėnas and
• Sigitas Tumkevicius

Beilstein J. Org. Chem. 2022, 18, 497–507, doi:10.3762/bjoc.18.52

• -withdrawing groups, namely cyano, bromo or sulfonyl groups were introduced directly or through a phenylene bridge into position 2 of the pyrimidine ring. Results and Discussion Synthesis Due to the versatile reactivity of a methylthio group in the pyrimidine nucleus [34][35] we used 4,6-bis(3,6-di-tert-butyl

Recent advances in organocatalytic asymmetric aza-Michael reactions of amines and amides

• Pratibha Sharma,
• Raakhi Gupta and
• Raj K. Bansal

Beilstein J. Org. Chem. 2021, 17, 2585–2610, doi:10.3762/bjoc.17.173

• )benzenesulfonamides 115 using the same pyrrolidine catalyst 113. The products were obtained in excellent yields and enantioselectivities (Table 27) [68]. In this context, the presence of a strong electron-withdrawing sulfonyl group was found to be essential. On comparing efficacies of different sulfonyl groups

AgNTf₂-catalyzed formal [3 + 2] cycloaddition of ynamides with unprotected isoxazol-5-amines: efficient access to functionalized 5-amino-1H-pyrrole-3-carboxamide derivatives

• Ziping Cao,
• Jiekun Zhu,
• Li Liu,
• Yuanling Pang,
• Laijin Tian,
• Xuejun Sun and
• Xin Meng

Beilstein J. Org. Chem. 2019, 15, 2623–2630, doi:10.3762/bjoc.15.255

• 10ka–na were obtained in 50–98% yields. In addition, the Ts protecting group could be changed for other sulfonyl groups such as Ms (10na, 98%), o-Ns (10oa, 99%) and p-Ns (10pa, 99%), while the cyclic carbamate-derived ynamides such as 4q are no good substrates, leading to the formation of a complex

An efficient and concise access to 2-amino-4H-benzothiopyran-4-one derivatives

• Peng Li,
• Yongqi Wu,
• Tingting Zhang,
• Chen Ma,
• Ziyun Lin,
• Gang Li and
• Haihong Huang

Beilstein J. Org. Chem. 2019, 15, 703–709, doi:10.3762/bjoc.15.65

• be the optimum leaving group by thorough investigations on the elimination of sulfide, sulfinyl, and sulfonyl groups at the 2-position of benzothiopyranone. Most 2-aminobenzothiopyranones were obtained in good to excellent yields under refluxing in isopropanol within 36 h. This method is base-free

• substituent leading to 2-methylamino-3-cyanobenzothiopyranones was disclosed by Rudorf and co-workers (method C, Scheme 1) [9]. Recently, a similar strategy was successfully utilized to afford N-substituted 2-aminobenzothiopyranones through the replacement of sulfide, sulfinyl or sulfonyl groups with amines

• -imidazolylbenzothiopyranones [10]. It is well known that the sulfide, sulfinyl and sulfonyl groups are generally used as the leaving group for the synthesis of 2-substituted 4H-chromen-4-ones [11][12][13][14][15][16][17][18][19][20][21][22]. Due to the higher electronegativity of the oxygen atom compared to the sulfur atom

Enhanced single-isomer separation and pseudoenantiomer resolution of new primary rim heterobifunctionalized α-cyclodextrin derivatives

• Iveta Tichá,
• Gábor Benkovics,
• Milo Malanga and
• Jindřich Jindřich

Beilstein J. Org. Chem. 2018, 14, 2829–2837, doi:10.3762/bjoc.14.261

• ´-disulfonyl chloride. The prepared 6A,6X-disulfonyl-capped CDs 2 and 3 were immediately converted to the more stable 6A,6X-diazido-α-CDs 4 to prevent hydrolysis. However, the yields were low because the hydrolysis of sulfonyl groups could not be completely suppressed. The prepared 6A,6X-diazido-α-CDs were

Facile synthesis of 4H-chromene derivatives via base-mediated annulation of ortho-hydroxychalcones and 2-bromoallyl sulfones

• Srinivas Thadkapally,
• Athira C. Kunjachan and
• Rajeev S. Menon

Beilstein J. Org. Chem. 2016, 12, 16–21, doi:10.3762/bjoc.12.3

• carbonyl and sulfonyl groups are easily incorporated into the privileged scaffold of 4H-chromene via this method. 4H-chromene (1) and some of its biologically active derivatives. a) Preparation of 2-bromoallyl sulfones 2a,b; b) reaction of 2a with 4-chlorophenol and Cs2CO3; c) reaction of 2a with

Pd/C- Mediated synthesis of indoles in water

• Mohosin Layek,
• Udaya Lakshmi,
• Dipak Kalita,
• Deepak K. Barange,
• Aminul Islam,
• K. Mukkanti and
• Manojit Pal

Beilstein J. Org. Chem. 2009, 5, No. 46, doi:10.3762/bjoc.5.46

• . a methyl group on the o-iodoaniline ring was examined. Moreover, the presence of other sulfonyl groups e.g. the benzenesulfonyl moiety on the aniline nitrogen was not studied. In the present study we aimed to conduct further research taking into account of above-mentioned aspects. Thus, when o

Reduction of arenediazonium salts by tetrakis(dimethylamino)ethylene (TDAE): Efficient formation of products derived from aryl radicals

• Mohan Mahesh,
• John A. Murphy,
• Franck LeStrat and
• Hans Peter Wessel

Beilstein J. Org. Chem. 2009, 5, No. 1, doi:10.3762/bjoc.5.1

• the radical chemistry. One way to achieve clean termination of the radical process would be by providing a radical leaving group adjacent to the cyclised radical 19. Appropriate groups might be sulfide, sulfoxide and sulfonyl groups [64][65]. Accordingly, arenediazonium salts 31a–d were prepared