Zinc(II)-Catalyzed Synthesis of Secondary Amides from Ketones via Beckmann Rearrangement Using Hydroxylamine-O-sulfonic Acid in Aqueous Media

Saumya Verma; Puneet Kumar; Anil K. Khatana; Dinesh Chandra; Ajay K. Yadav; Bhoopendra Tiwari; Jawahar L. Jat

doi:10.1055/s-0040-1707809

Synthesis, Inhaltsverzeichnis

Synthesis 2020; 52(21): 3272-3276
DOI: 10.1055/s-0040-1707809

special topic

Zinc(II)-Catalyzed Synthesis of Secondary Amides from Ketones via Beckmann Rearrangement Using Hydroxylamine-O-sulfonic Acid in Aqueous Media

Saumya Verma

^aDepartment of Chemistry, Babasaheb Bhimrao Ambedkar University (A Central University), Lucknow, India eMail: jawaharlj@bbau.ac.in eMail: jatjawahar@gmail.com

,

Puneet Kumar

^aDepartment of Chemistry, Babasaheb Bhimrao Ambedkar University (A Central University), Lucknow, India eMail: jawaharlj@bbau.ac.in eMail: jatjawahar@gmail.com

,

Anil K. Khatana

^bDivision of Molecular Synthesis & Drug Discovery, Centre of Biomedical Research, SGPGIMS-Campus, Raebareli Road, Lucknow, India

,

Dinesh Chandra

^aDepartment of Chemistry, Babasaheb Bhimrao Ambedkar University (A Central University), Lucknow, India eMail: jawaharlj@bbau.ac.in eMail: jatjawahar@gmail.com

,

Ajay K. Yadav

^aDepartment of Chemistry, Babasaheb Bhimrao Ambedkar University (A Central University), Lucknow, India eMail: jawaharlj@bbau.ac.in eMail: jatjawahar@gmail.com

,

Bhoopendra Tiwari

^bDivision of Molecular Synthesis & Drug Discovery, Centre of Biomedical Research, SGPGIMS-Campus, Raebareli Road, Lucknow, India

,

Jawahar L. Jat ∗

^aDepartment of Chemistry, Babasaheb Bhimrao Ambedkar University (A Central University), Lucknow, India eMail: jawaharlj@bbau.ac.in eMail: jatjawahar@gmail.com

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Abstract

Alle Artikel dieser Rubrik

Published as part of the Special Topic Recent Advances in Amide Bond Formation

Abstract

A zinc(II)-catalyzed single-step protocol for the Beckmann rearrangement using hydroxylamine-O-sulfonic acid (HOSA) as the nitrogen source in water was developed. This direct method efficiently produces secondary amides under open atmosphere in a pure form after basic aqueous workup. It is environmentally benign and operationally simple.

Key words

zinc(II) chloride - hydroxylamine-O-sulfonic acid (HOSA) - ketones - Beckmann rearrangement - amides

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Referenzen

References

1a Krow GR. Tetrahedron 1981; 37: 1283
1b Palmer RJ. Encyclopedia of Polymer Science and Technology, 4th ed. Wiley; New York: 2001
1c Greenberg A, Breneman CM, Liebman JF. The Amide Linkage: Structural Significance in Chemistry, Biochemistry, and Materials Science. John Wiley & Sons; New York: 2003
1d Carey JS, Laffan D, Thomson C, Williams MT. Org. Biomol. Chem. 2006; 4: 2337
1e Tani K, Stoltz BM. Nature 2006; 441: 731
1f You K, Mao L, Yin D, Liu P, Luo H. Catal. Commun. 2008; 9: 1521
1g Pattabiraman VR, Bode JW. Nature 2011; 480: 471
1h Roughley SD, Jordan AM. J. Med. Chem. 2011; 54: 3451
1i Liu C, Szostak M. Chem. Eur. J. 2017; 23: 7157
1j Dander JE, Garg NK. ACS Catal. 2017; 7: 1413
1k Sui G, Xu D, Luo T, Guo H, Sheng G, Yin D, Ren L, Hao H, Zhou W. Bioorg. Med. Chem. Lett. 2020; 30: 126774

2a Wang C, Jiang X, Shi H, Lu J, Hu Y, Hu H. J. Org. Chem. 2003; 68: 4579
2b Ichino T, Arimoto H, Uemura D. Chem. Commun. 2006; 16: 1742
2c DeRosa TF. Amides. Advances in Synthetic Organic Chemistry and Methods Reported in US Patents. Elsevier; Amsterdam: 2006
2d Kumar R, Wadhwa D, Prakash O. Heterocycl. Commun. 2010; 16: 201
2e Saeki M, Toyota M. Tetrahedron Lett. 2010; 51: 4620
2f Zeng R, Fu C, Ma S. J. Am. Chem. Soc. 2012; 134: 9597
2g Kaiser D, Bauer A, Lemmerer M, Maulide N. Chem. Soc. Rev. 2018; 47: 7899
2h Sato T, Yoritate M, Tajima H, Chida N. Org. Biomol. Chem. 2018; 16: 3864
2i Zheng Q, Liu C.-F, Chen J, Rao G.-W. Adv. Synth. Catal. 2020; 362: 1406

3a El-Faham A, Albericio F. Chem. Rev. 2011; 111: 6557
3b Lanigan RM, Sheppard TD. Eur. J. Org. Chem. 2013; 7453
3c De Figueiredo RM, Suppo J.-S, Campagne J.-M. Chem. Rev. 2016; 116: 12029
3d Ojeda-Porras A, Gamba-Sánchez D. J. Org. Chem. 2016; 81: 11548
3e Treitler DS, Marriott AS, Chadwick J, Quirk E. Org. Process Res. Dev. 2019; 23: 2562
3f Nagaraaj P, Vijayakumar V. Org. Chem. Front. 2019; 6: 2570

4a Beckmann E. Ber. Dtsch. Chem. Ges. 1886; 19: 988
4b Blatt AH. Chem. Rev. 1933; 12: 215
4c Gawley RE. Org. React. 1988; 35: 1
4d Smith MB, March J. Advanced Organic Chemistry, 5th ed. Wiley; New York: 2001: 1415 ; and references cited therein
4e Chandrasekhar S. The Beckmann and Related Reactions. In Comprehensive Organic Synthesis II, Vol. 7. Knochel P, Molander GA. Elsevier; Amsterdam: 2014. Chap. 7.25, 770-800
4f Debnath P. Curr. Org. Synth. 2018; 15: 666

5a Arisawa M, Yamaguchi M. Org. Lett. 2001; 3: 311
5b Furuya Y, Ishihara K, Yamamoto H. J. Am. Chem. Soc. 2005; 127: 11240
5c Ramalingan C, Park Y.-T. J. Org. Chem. 2007; 72: 4536
5d Betti C, Landini D, Maia A, Pasi M. Synlett 2008; 908
5e Srivastava VP, Yadav AK, Yadav LD. S. Synlett 2014; 25: 665
5f Kiely-Collins HJ, Sechi I, Brennan PE, McLaughlin MG. Chem. Commun. 2018; 54: 654
5g Zhang W, Yang S, Lin Q, Cheng H, Liu J. J. Org. Chem. 2019; 84: 851
5h See also refs. 9–16

6a Olah GA, Fung AP. Synthesis 1979; 537
6b Sharghi H, Hosseini M. Synthesis 2002; 1057
6c Mahajan S, Sharma B, Kapoor KK. Tetrahedron Lett. 2015; 56: 1915
6d Hyodo K, Hasegawa G, Oishi N, Kuroda K, Uchida K. J. Org. Chem. 2018; 83: 13080
6e Jain PU, Samant SD. ChemistrySelect 2018; 3: 1967
6f Chandra D, Verma S, Pandey CB, Yadav AK, Kumar P, Tiwari B, Jat JL. Tetrahedron Lett. 2020; 61: 151822

7 Munnuri S, Verma S, Chandra D, Anugu RR, Falck JR, Jat JL. Synthesis 2019; 51: 3709

8a Wallace RG. Aldrichimica Acta 1980; 13: 3
8b Erdik E., Saczewski J.; Hydroxylamine-O-sulfonic Acid, In Encyclopedia of Reagents for Organic Synthesis; John Wiley & Sons: New York, 2013; doi: 10.1002/047084289X.rh058.pub2

9 Mo X, Morgan TD. R, Ang HT, Hall DG. J. Am. Chem. Soc. 2018; 140: 5264
10 Hashimoto M, Obora Y, Sakaguchi S, Ishii Y. J. Org. Chem. 2008; 73: 2894
11 Schmidt B, Wolf F. J. Org. Chem. 2017; 82: 4386
12 An N, Tian B.-X, Pi H.-J, Eriksson LA, Deng W.-P. J. Org. Chem. 2013; 78: 4297
13 Schulz L, Enders M, Elsler B, Schollmeyer D, Dyballa KM, Franke R, Waldvogel SR. Angew. Chem. Int. Ed. 2017; 56: 4877
14 Singh H, Sen C, Sahoo T, Ghosh SC. Eur. J. Org. Chem. 2018; 34: 4748
15 Gao Y, Liu J, Li Z, Guo T, Xu S, Zhu H, Wei F, Chen S, Gebru H, Guo K. J. Org. Chem. 2018; 83: 2040
16 Steffel LR, Cashman TJ, Reutershan MH, Linton BR. J. Am. Chem. Soc. 2007; 129: 12956

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