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1. Synthesis of (Z)-β-Chloro-enamides via a Base-Promoted trans-Hydroamidation of Alkynyl Chlorides Using 1,1-Dichloroalkenes as Precursor

Author:
Zhenming Zhang; Bei Fu; Xiaoshuo Wang; Zhipeng Hu; Xuanling Liu; Tao Wang; Junfeng Zhao
Source:
Journal of organic chemistry 2022 v.87 no.13 pp. 8764-8772
ISSN:
1520-6904
Subject:
sulfonamides,   etc   ; journals; organic chemistry; stereoselectivity;     Show all 4 Subjects
Abstract:
... An efficient and general base-promoted reaction of 1,1-dichloroalkenes with secondary sulfonamides and amides for the synthesis of (Z)-β-chloro-enamides has been described. This reaction exhibits functional group tolerance under simple and mild conditions. Mechanistic study indicated that a stereoselective trans-hydroamidation of alkynyl chlorides generated in situ from 1,1-dichloroalkenes was the ...
DOI:
10.1021/acs.joc.2c00581

2. A practical method for N-cyanation of secondary amines and sulfonamides

Author:
Zhaojun Hang; Xiaowei Tong; Zuowa Li; Zhao-yan Wang; Weihua Xue
Source:
Tetrahedron letters 2022 v.88 pp. 153564
ISSN:
0040-4039
Subject:
sulfonamides,   etc   ; Lewis acids; cyanamides; methodology; secondary amines;     Show all 5 Subjects
Abstract:
... Cyanamides are an important class of molecules. This work describes a facile synthesis of disubstituted cyanamides. Here, readily accessible 1-cyano-1, 2-benziodoxol-3-(1H)-one (CBX) was applied as a stable electrophilic cyanation reagent. Diverse secondary amines were effectively cyanated. Moreover, secondary sulfonamides proved to be suitable substrates and were readily converted to N-alkyl(aryl ...
DOI:
10.1016/j.tetlet.2021.153564

3. Rapid Access to Aliphatic Sulfonamides

Author:
Mingjun Zhang; Mo Yu; Ziwen Wang; Yuxiu Liu; Qingmin Wang
Source:
Organic letters 2022 v.24 no.22 pp. 3932-3937
ISSN:
1523-7052
Subject:
sulfonamides,   etc   ; bioactive compounds; carboxylic acids; ethylation; medicine; methodology; skeleton; synthetic products; utilities;     Show all 9 Subjects
Abstract:
... Herein, we report a mild, rapid, straightforward method for visible-light-mediated sulfonamide ethylation to afford a diverse array of compounds with C(sp³)–sulfonamide skeletons. The method relies on inexpensive, abundant, commercially available primary, secondary, and tertiary alkyl carboxylic acids and alkyl iodides as substrates. The method has a broad substrate scope and potential utility for ...
DOI:
10.1021/acs.orglett.2c01236

4. Design, synthesis, and insecticidal activities of propargyloxy-naphthalene-sulfonamide derivatives

Author:
Wang-Yu Zhao; Chao-Fu Yang; Li-Juan Han; Bo Zhou; Ai-Juan Li; Lu-Lu Liu; Zi-Wei Zhang; Zi-Yu Wang; Wen-Jun Wu; Ji-Wen Zhang
Source:
Journal of Asian natural products research 2022 v.24 no.4 pp. 361-370
ISSN:
1477-2213
Subject:
sulfonamides,   etc   ; Asians; computer simulation; design; insecticidal properties; journals; pharmacodynamics; receptors; research; structure-activity relationships;     Show all 10 Subjects
Abstract:
... In our previous studies, a kind of novel benzenesulfonamides was found to be a candidate insecticidal compounds. It was shown that propargyloxy and sulfonamide groups are pharmacodynamic groups. One hundred and twenty-six (126) naphthalenesulfonamides derivatives with propargyloxy functionality were designed and synthesized, and their insecticidal activities were determined. Some of them showed ou ...
DOI:
10.1080/10286020.2021.1925254

5. Biaryl sulfonamides as cisoid azosteres for photopharmacology

Author:
Piermichele Kobauri; Wiktor Szymanski; Fangyuan Cao; Sebastian Thallmair; Siewert J. Marrink; Martin D. Witte; Frank J. Dekker; Ben L. Feringa
Source:
Chemical communications 2021 v.57 no.34 pp. 4126-4129
ISSN:
1364-548X
Subject:
sulfonamides,   etc   ; chemical communication; drugs;     Show all 3 Subjects
Abstract:
... Biaryl sulfonamides are excellent candidates for the azologization approach that yields photoswitchable drugs more active in their metastable cis state, compared to the stable trans state. Here we present the scope and limitations of this strategy for rational design in photopharmacology. ...
DOI:
10.1039/d1cc00950h

6. Hexafluoroisopropanol (HFIP)-prompted rearrangement of N-phenoxysulfonamides for the direct assembly of ortho-sulfonamide phenols: A combined experimental and computational study

Author:
Yi Wang; Xiaoli Chen; Shuang Lin; Hui Gao; Fu-Xiaomin Liu; Zhi Zhou; Wei Yi
Source:
Tetrahedron letters 2022 v.89 pp. 153601
ISSN:
0040-4039
Subject:
sulfonamides,   etc   ; hydrogen bonding; phenol; regioselectivity;     Show all 4 Subjects
Abstract:
... ortho-Sulfonamide phenols represent a class of attractive structural motifs in medicinal and synthetic chemistry. Herein an efficient metal-free rearrangement reaction has been developed for the construction of ortho-sulfonamide phenols via HFIP-prompted intramolecular sulfonamide group 1,3-migration. This protocol features mild reaction conditions, broad functional group compatibility and good re ...
DOI:
10.1016/j.tetlet.2021.153601

7. Rapid Access to N-Protected Sulfonimidoyl Fluorides: Divergent Synthesis of Sulfonamides and Sulfonimidamides

Author:
Yongan Liu; Qijun Pan; Xiaojun Hu; Yong Guo; Qing-Yun Chen; Chao Liu
Source:
Organic letters 2021 v.23 no.10 pp. 3975-3980
ISSN:
1523-7052
Subject:
sulfonamides,   etc   ; bioactive compounds; fluorides; salting;     Show all 4 Subjects
Abstract:
... Herein we report a practical and efficient copper-catalyzed approach for the conversion of various arenediazonium salts to the corresponding N-protected sulfonimidoyl fluorides. This operationally simple protocol tolerates a wide range of functional groups and can be applied to the late-stage modification of complex bioactive molecules. Furthermore, pharmaceutically important primary sulfonamides ...
DOI:
10.1021/acs.orglett.1c01118

8. Photoredox-Mediated Mono- and Difluorination of Remote Unactivated Methylene C(sp³)–H Bonds of N-Alkyl Sulfonamides

Author:
Zhiqiang Deng; Zhenxiang Zhao; Gang He; Gong Chen
Source:
Organic letters 2021 v.23 no.9 pp. 3631-3635
ISSN:
1523-7052
Subject:
sulfonamides,   etc   ; amines; free radicals; oxidation;     Show all 4 Subjects
Abstract:
... A photoredox-mediated δ-C(sp³)–H fluorination of sulfonyl-protected primary alkylamines with Selectfluor is developed. The reaction can proceed in excellent monofluorination selectivity for amine substrates without α substituent. For α-substituted substrates, a slightly modified reaction conditions with two rounds of operation gives the δ,δ-difluorination products in good yield. Mechanistic studie ...
DOI:
10.1021/acs.orglett.1c01020

9. Palladium-Catalyzed Domino Heck/Sulfination: Synthesis of Sulfonylated Hetero- and Carbocyclic Scaffolds Using DABCO–Bis(sulfur dioxide)

Author:
Jonathan Bajohr; Abdoul G. Diallo; Andrew Whyte; Sylvain Gaillard; Jean-Luc Renaud; Mark Lautens
Source:
Organic letters 2021 v.23 no.7 pp. 2797-2801
ISSN:
1523-7052
Subject:
sulfonamides,   etc   ; chemical reactions; gases; sulfur dioxide;     Show all 4 Subjects
Abstract:
... The synthesis of a broad variety of hetero- and carbocyclic scaffolds via a Pd-catalyzed domino Heck/SO₂ insertion reaction is reported. This reaction utilizes DABSO, a safe and easy-to-handle alternative to SO₂ gas. The reaction proceeds through a sulfinate intermediate, which can act as a lynchpin for the in situ generation of sulfones, sulfonamides, and sulfonyl fluorides. Good yields and scala ...
DOI:
10.1021/acs.orglett.1c00716

10. Traceless selenocarboxylates for the one-pot synthesis of amides and derivatives

Author:
Luana Silva; Alisson R. Rosário; Bianca M. Machado; Diogo S. Lüdtke
Source:
Tetrahedron 2021 v.79 pp. 131834
ISSN:
0040-4020
Subject:
sulfonamides,   etc   ; fatty acids; heterocyclic compounds; imides; synthesis;     Show all 5 Subjects
Abstract:
... We have recently reported a one-pot procedure for glycosyl amides synthesis using selenocarboxylate as traceless reagent. Herein, we present a further application of selenocarboxylate-azide reaction for amide bond formation on a broader range of substrates, including heterocyclic systems and fatty acid. This method proved to be highly efficient for the synthesis of primary and secondary amides, su ...
DOI:
10.1016/j.tet.2020.131834

11. Resolving alternative structure determinations of indapamide using ¹³C solid-state NMR

Author:
Caitlin L. Evans; Ivana Radosavlijević Evans; Paul Hodgkinson
Source:
Chemical communications 2022 v.58 no.30 pp. 4767-4770
ISSN:
1364-548X
Subject:
sulfonamides,   etc   ; chemical communication; crystal structure; databases; diuretics; exhibitions;     Show all 6 Subjects
Abstract:
... The conflict between alternative crystal structures in the Cambridge Structural Database for the diuretic drug indapamide hemihydrate (IND) has been resolved with the aid of ¹³C solid-state NMR. IND is seen to contain multiple distinct molecules in the asymmetric unit (Z′ = 4) rather than exhibiting disorder in the orientation of sulfonamide groups. The NMR crystallographic approach is a more effe ...
DOI:
10.1039/d1cc06256e

12. Nickel-mediated C(sp2)-H amidation in synthesis of secondary sulfonamides via sulfonyl azides as amino source

Author:
Peng Xu; Peng-Fei Ding; Mei-Qi Zhang; Yu-Shi Xia; Ting Xie
Source:
Tetrahedron letters 2021 v.66 pp. 152825
ISSN:
0040-4039
Subject:
sulfonamides,   etc   ; amines; azides; catalytic activity; exhibitions; fields; methodology;     Show all 7 Subjects
Abstract:
... In this paper, Ni(II)- Catalyzed ortho-amidation of C(sp²)-H bond with sulfonyl azides directed by (quinolin-8-yl) amine (AQ-amine) is described. The method provides a straightforward method for the synthesis of sulfonamides from available sulfonyl azides via the transition-metal-catalyzed C(sp²)-N bond forming reaction. The amidation reactions exhibit high functional group compatibility, which mi ...
DOI:
10.1016/j.tetlet.2021.152825

13. Regio- and diastereoselective synthesis of trans-3,4-diaryldihydrocoumarins via metal-free [4+2] annulation of ynamides with o-hydroxybenzyl alcohols

Author:
Wen-Feng Luo; Long-Wu Ye; Long Li; Peng-Cheng Qian
Source:
Chemical communications 2021 v.57 no.41 pp. 5032-5035
ISSN:
1364-548X
Subject:
sulfonamides,   etc   ; alcohols; chemical communication; diastereoselective synthesis; diastereoselectivity; methodology;     Show all 6 Subjects
Abstract:
... An efficient regio- and diastereoselective method for the construction of valuable trans-3,4-diaryldihydrocoumarins via metal-free [4+2] annulation of ynamides with o-hydroxybenzyl alcohols has been developed. Ynamides are first treated as 2–π partners to react with o-hydroxybenzyl alcohols via traceless sulfonamide directing groups, affording trans-3,4-diaryldihydrocoumarins in good yields with h ...
DOI:
10.1039/d1cc00687h

14. Mechanochemical Conversion of Aromatic Amines to Aryl Trifluoromethyl Ethers

Author:
Michał Jakubczyk; Satenik Mkrtchyan; Mohanad Shkoor; Suneel Lanka; Šimon Budzák; Miroslav Iliaš; Marek Skoršepa; Viktor O. Iaroshenko
Source:
Journal of the American Chemical Society 2022 v.144 no.23 pp. 10438-10445
ISSN:
1520-5126
Subject:
sulfonamides,   etc   ; Americans; aniline; ethers; journals; mechanochemistry; methodology; pharmaceutical industry;     Show all 8 Subjects
Abstract:
... Increased interest in the trifluoromethoxy group in organic synthesis and medicinal chemistry has induced a demand for new, selective, general, and faster methods applicable to natural products and highly functionalized compounds at a later stage of hit-to-lead campaigns. Applying pyrylium tetrafluoroborate, we have developed a mechanochemical protocol to selectively substitute the aromatic amino ...
DOI:
10.1021/jacs.2c02611

15. Visible-Light-Mediated Late-Stage Sulfonylation of Anilines with Sulfonamides

Author:
Xiao-Hong Xu; Jing-Song Zhen; Xian Du; Han Yuan; Yi-Hui Li; Man-Hei Chu; Yong Luo
Source:
Organic letters 2022 v.24 no.3 pp. 853-858
ISSN:
1523-7052
Subject:
sulfonamides,   etc   ; aniline; carbon-hydrogen bond activation; drugs; sulfonylation; utilities;     Show all 6 Subjects
Abstract:
... A visible-light-mediated late-stage sulfonylation of anilines with sulfonamides under simple reaction conditions is presented. Various primary or secondary sulfonamides including several pharmaceuticals were incorporated successfully via N–S bond activation and C–H bond sulfonylation. The synthetic utility of this strategy is highlighted by the construction of complex anilines bearing diverse bioa ...
DOI:
10.1021/acs.orglett.1c04144

16. Strategies of modifying spiro-OMeTAD materials for perovskite solar cells: a review

Author:
Guanhua Ren; Wenbin Han; Yanyu Deng; Wei Wu; Zhuowei Li; Jiaxin Guo; Hongchang Bao; Chunyu Liu; Wenbin Guo
Source:
Journal of materials chemistry A 2021 v.9 no.8 pp. 4589-4625
ISSN:
2050-7496
Subject:
sulfonamides,   etc   ; hygroscopicity; ions; journals; lithium; materials; salting; salts; solar cells;     Show all 9 Subjects
Abstract:
... Organic–inorganic hybrid perovskite solar cells (PSCs) have made unprecedented progress in the past ten years, the power conversion efficiency of which increased from 3.8% in 2009 to 25.5% in 2020. The choice of hole transport layers (HTLs) is a key factor for achieving efficient and stable PSCs. Recently, 2,2′,7,7′-tetrakis-(N,N-di-4-methoxyphenylamino)-9,9′-spirobifluorene (spiro-OMeTAD) has bee ...
DOI:
10.1039/d0ta11564a

17. Mechanochemical synthesis of aromatic sulfonamides

Author:
Satenik Mkrtchyan; Viktor O. Iaroshenko
Source:
Chemical communications 2021 v.57 no.84 pp. 11029-11032
ISSN:
1364-548X
Subject:
sulfonamides,   etc   ; aromatic acids; aromatic amines; carboxylic acids; chemical communication; mechanochemistry; primary energy;     Show all 7 Subjects
Abstract:
... A three-component Pd-catalysed aminosulfonylation reaction of K₂S₂O₅ and amine with aryl bromides or aromatic carboxylic acids was developed. This strategy was developed to utilise mechanical energy and accommodate primary as well as secondary aliphatic and aromatic amines to provide a new shortcut to a wide range of sulfonamides. Studies on the scope and limitations of the reaction indicated its ...
DOI:
10.1039/d1cc03224k

18. Novel 3,4-dihydro-1,4-oxazine (dehydromorpholine) sulfonamides and sulfones conveniently accessed from suitable a-diazoketones via O[sbnd]H carbene insertion – Cyclization sequence

Author:
Igor Solovyev; Dmitry Dar'in; Mikhail Krasavin
Source:
Tetrahedron letters 2021 v.78 pp. 153269
ISSN:
0040-4039
Subject:
sulfonamides,   etc   ; bromine; carbenes; primary amines;     Show all 4 Subjects
Abstract:
... A short and practically convenient, modular approach to hitherto unknown dehydromorpholine sulfones and sulfonamides from α-acyl-α-diazomethyl sulfones and sulfonamides, respectively, has been developed. It involves Rh(II) carbene insertion into the OH bond of 2-bromoethanol followed by thermally promoted tandem SN2 displacement of the bromine atom by a primary amine and cyclodehydration. ...
DOI:
10.1016/j.tetlet.2021.153269

19. Facile assembly of 1,5-diazocan-2-ones via cyclization of tethered sulfonamides to cyclopropenes

Author:
Jonathon P. Matheny; Pavel M. Yamanushkin; Peter A. Petillo; Michael Rubin
Source:
RSC advances 2020 v.10 no.72 pp. 44183-44190
ISSN:
2046-2069
Subject:
sulfonamides,   etc   ; Lewis bases; amines; moieties;     Show all 4 Subjects
Abstract:
... The sulfonamide moiety was evaluated as an activating and stabilizing functional group in the metal-templated strain release-driven intramolecular nucleophilic addition of amines to cyclopropenes to generate 1,5-diazocan-2-ones. ...
DOI:
10.1039/d0ra09014j

20. Enantioselective Copper-Catalyzed Remote C(sp³)–H Alkynylation of Linear Primary Sulfonamides

Author:
Cheng-Yu Wang; Zi-Yang Qin; Yu-Ling Huang; Yi-Ming Hou; Ruo-Xing Jin; Chao Li; Xi-Sheng Wang
Source:
Organic letters 2020 v.22 no.10 pp. 4006-4009
ISSN:
1523-7052
Subject:
sulfonamides,   etc   ; alkynes; enantioselectivity; free radicals; methodology;     Show all 5 Subjects
Abstract:
... The highly efficient copper-catalyzed enantioselective alkynylation of the remote C(sp³)–H bond on linear primary sulfonamides is presented here using a radical relay strategy. The chiral box–copper complex, which is used to recapture the in-situ-generated alkyl radical via a 1,5-HAT strategy, is the key to success, affording the chiral alkynes after a following reductive elimination. A general su ...
DOI:
10.1021/acs.orglett.0c01325