Zn/ZnBr2 Catalysed Reaction of Aldehydes with Allylbromide: Synthesis of 2,6-Disubstituted 4-Bromotetrahydropyrans

D. O. Biradar; Y. D. Mane; Y. P. Sarnikar; S. G. Kulkarni; B. V. Subba Reddy; A. Venkat Narsaiah

doi:10.1055/s-0042-1751374

SynOpen, Table of Contents

CC BY-NC-ND 4.0 · SynOpen 2022; 06(04): 263-269
DOI: 10.1055/s-0042-1751374

paper

Zn/ZnBr₂ Catalysed Reaction of Aldehydes with Allylbromide: Synthesis of 2,6-Disubstituted 4-Bromotetrahydropyrans

Authors

D. O. Biradar

^aOrganic Synthesis Laboratory, Fluoro-Agrochemicals Department, CSIR-Indian Institute of Chemical Technology, Hyderabad-500007, Telangana, India
Y. D. Mane

^bBSS Arts, Science & Commerce College, Makni Tq, Lohara-413604, Osmanabad, MS, India
Y. P. Sarnikar

^cDayanand Science College, Latur-413512, MS, India
S. G. Kulkarni

^dMaharastra Mahavidyalaya, Nilanga-413521, MS, India
B. V. Subba Reddy

^aOrganic Synthesis Laboratory, Fluoro-Agrochemicals Department, CSIR-Indian Institute of Chemical Technology, Hyderabad-500007, Telangana, India
A. Venkat Narsaiah ∗

^aOrganic Synthesis Laboratory, Fluoro-Agrochemicals Department, CSIR-Indian Institute of Chemical Technology, Hyderabad-500007, Telangana, India

Abstract

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Abstract

An efficient approach for the one-pot synthesis of 4-bromotetrahydropyrans in a highly diastereoselective manner via the alkynylation followed by Prins cyclisation is described. The method employs aldehydes and allyl bromide as reactants, with a Zn/ZnBr₂ catalytic system in CH₂Cl₂. A variety of 2,6-disubstituted 4-bromotetrahydropyran derivatives were obtained in good yields.

Key words

Prins cyclisation - tetrahydropyrans - aldehydes - allylbromides - one-pot reaction

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References

References

1a Martín T, Padrón JI, Martín VS. Synlett 2014; 25: 12
1b Nicolaou KC, Sorenson EJ. Classics in Total Synthesis. VCH Weinheim. 1969
1c Reddy UC, Raju BR, Kumar EK. P, Saikia AK. J. Org. Chem. 2008; 73: 1628
1d Yoshimitsu T, Makino T, Nagaoka H. J. Org. Chem. 2004; 69: 1993
1e Lee J, Oh HS, Kang HY. Tetrahedron Lett. 2015; 56: 1099
1f Norcross RD, Paterson I. Chem. Rev. 1995; 95: 2041
1g Tian X, Jaber JJ, Rychnovsky SD. J. Org. Chem. 2006; 71: 3176
1h Yang XF, Wang M, Zhang Y, Li CJ. Synlett 2005; 1912

2a Su BN, Takaishi Y, Kusumi T, Morinols AL. Tetrahedron 1999; 55: 14571
2b Yamauchi S, Kawahara S, Wukirsari T, Nishiwaki H, Nishi K, Sugahara T, Akiyama K, Kishida T. Bioorg. Med. Chem. Lett. 2013; 23: 4923
2c Akiyama K, Yamauchi S, Maruyama M, Sugahara T, Kishida T, Koba Y. Biosci., Biotechnol., Biochem. 2009; 73: 129
2d Masuda K, Nishiwaki H, Akiyama K, Yamauchi S, Maruyama M, Sugahara T, Kishida T. Biosci., Biotechnol., Biochem. 2010; 74: 2071

3a Ghosh AK, Anderson DD. Future Med. Chem. 2011; 3: 1181
3b Capim SL, Gonçalves GM, dos Santos GC. M, Marinho BG, Vasconcellos ML. A. A. Bioorg. Med. Chem. 2013; 21: 6003
3c Capim SL, Carneiro PH. P, Castro PC, Barros MR. M, Marinho BG, Vasconcellos ML. A. A. Eur. J. Med. Chem. 2012; 58: 1
3d Kharkar PS, Reith ME. A, Dutta AK. J. Comput.-Aided Mol. Des. 2008; 22: 1

4a Surivet JP, Zumbrunn C, Rueedi G, Bur D, Bruyère T, Locher H, Ritz D, Seiler P, Kohl C, Ertel EA, Hess P, Gauvin JC, Mirre A, Kaegi V, dos Santos M, Kraemer S, Gaertner M, Delers J, Enderlin PM, Weiss M, Sube R, Hadana H, Keck W, Hubschwerlen C. J. Med. Chem. 2015; 58: 927
4b Surivet JP, Zumbrunn C, Bruyère T, Bur D, Kohl C, Locher HH, Seiler P, Ertel EA, Hess P, Enderlin PM, Enderlin PS, Gauvin JC, Mirre A, Hubschwerlen C, Ritz D, Rueedi G. J. Med. Chem. 2017; 60: 3776

5a León LG, Miranda PO, Martín VS, Padrón JI, Padrón JM. Bioorg. Med. Chem. Lett. 2007; 17: 2681
5b Carrillo R, León LG, Martín T, Martín VS, Padrón JM. Bioorg. Med. Chem. Lett. 2007; 17: 780
5c Miranda PO, León LG, Martín VS, Padrón JI, Padrón JM. Bioorg. Med. Chem. Lett. 2006; 16: 3135

6a Muzart J. J. Mol. Catal. A: Chem. 2010; 319: 1
6b Smith AB. III, Fox RJ, Razler T. Acc. Chem. Res. 2008; 41: 675
6c Larrosa I, Romea P, Urpí F. Tetrahedron 2008; 64: 2683
6d Boivin TL. B. Tetrahedron 1987; 43: 3309
6e Nasir NM, Ermanis K, Clarke PA. Org. Biomol. Chem. 2014; 12: 3323
6f Clarke PA, Santos S. Eur. J. Org. Chem. 2006; 2045

7 McDonald BR, Scheidt KA. Acc. Chem. Res. 2015; 48: 1172

8a Yamazaki S, Fujinami K, Maitoko Y, Ueda K, Kakiuchi K. J. Org. Chem. 2013; 78: 8405
8b Yadav VK, Verma AK, Kumar P, Hulika V. Chem. Commun. 2014; 50: 15457
8c Budakoti A, Mondal PK, Verma P, Khamrai J. Beilstein J. Org. Chem. 2021; 17: 932
8d Padmaja P, Reddy PN, Reddy BV. S. Org. Biomol. Chem. 2020; 18: 7514
8e Reddy BV. S, Nair PN, Antony A, Srivastava N. Eur. J. Org. Chem. 2017; 5484

9a Wang D, Zhao X, Liu L, Chen YJ. Tetrahedron 2006; 62: 7113
9b Poliane KB, JoãoMarcos G, deFerreira O, Fabio PL, Silva ML. A, Vasconcellos A, Juliana AV. Molecules 2019; 24: 2084
9c Wen M, Tang L, Chang W, Li J. Sci. China, Ser. B: Chem. 2005; 48: 38

10a Konakanchi R, Kankala S, Kotha LR. Synth. Commun. 2018; 48: 1777
10b Wu XF. Chem. Asian J. 2012; 7: 2502
10c Wu XF, Neumann H. Adv. Synth. Catal. 2012; 354: 3141
10d Enthaler S. ACS Catal. 2013; 3: 150
10e Zhu A, Li L, Wang J, Zhuo K. Green Chem. 2011; 13: 1244
10f Cheung CW, Zhurkin FE, Hu X. J. Am. Chem. Soc. 2015; 137: 4932
10g Barzanò G, Cheseaux A, Hu X. Org. Lett. 2019; 21: 490

11 Miranda LS. M, Vasconcellos ML. A. A. Synthesis 2004; 1767

Supplementary Material

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