Complementary and Regioselective Synthesis of Isomeric 3-[Isoxazol-3(or 5)-yl]indoles from β-Ethylthio-β-indolyl-α,β-unsaturated Ketones

Haifeng Yu; Kehua Wang; Xue Zhang; Wenju Wang

doi:10.1055/s-0040-1706658

Synthesis, Table of Contents

Synthesis 2021; 53(11): 1989-1999
DOI: 10.1055/s-0040-1706658

paper

Complementary and Regioselective Synthesis of Isomeric 3-[Isoxazol-3(or 5)-yl]indoles from β-Ethylthio-β-indolyl-α,β-unsaturated Ketones

Haifeng Yu∗

^aCollege of Chemistry, Baicheng Normal University, Baicheng, Jilin 137000, China

,

Kehua Wang

^bSchool of Chemistry and Life Science, Anshan Normal University, Anshan, Liaoning, 114007, China

,

Xue Zhang

^aCollege of Chemistry, Baicheng Normal University, Baicheng, Jilin 137000, China

,

Wenju Wang∗

^aCollege of Chemistry, Baicheng Normal University, Baicheng, Jilin 137000, China

› Author Affiliations

Abstract

All articles of this category

Abstract

A simple and efficient method for the complementary and regioselective synthesis of isomeric 3-(isoxazol-5-yl)indoles and 3-(isoxazol-3-yl)indoles has been developed by the regioselective cyclocondensation reaction of β-ethylthio-β-indolyl-α,β-unsaturated ketones and hydroxylamine hydrochloride. It was found that the cyclocondensation reaction in the presence of excess NaOEt in refluxing EtOH gives 3-(isoxazol-5-yl)indoles in good yields, whereas using NaOAc in boiling AcOH gives 3-(isoxazol-3-yl)indoles in good yields.

Key words

unsaturated ketones - isoxazole - indole - hydroxylamine hydrochloride - regioselectivity - cyclocondensation reaction

Full Text

References

References
1 Matilda JJ, Reji AF. T. F. Asian J. Chem. 2020; 32: 244
2 Diana P, Carbone A, Barraja P, Kelter G, Fiebig HH, Cirrincione G. Bioorg. Med. Chem. 2010; 18: 4524
3 Somappa SB, Biradar JS, Rajesab P, Rahber S, Sundar M. Monatsh. Chem. 2015; 146: 2067
4 Rakesh KS, Jagadish S, Balaji KS, Zameer F, Swaroop TR, Mohan CD, Jayarama S, Rangappa KS. Inflammation 2016; 39: 269
5 Karp GC, Hwang PS, Takasugi JJ, Ren HY, Wilde RG, Turpoff AA, Arefolov A, Chen GM, Campbell JA. US 20070299069A1 2007
6 Sechi M, Sannia L, Carta F, Palomba M, Dallocchio R, Dessì A, Derudas M, Zawahir Z, Neamati N. Antiviral Chem. Chemother. 2005; 16: 41
7 Chirkova ZV, Filimonov SI, Abramov IG. Russ. Chem. Bull. 2017; 66: 1018
8 Biradar JS, Sharanbasappa B, Praveen SM, Sasidhar BS. Org. Chem.: Indian J. 2008; 4 (04) 266
9 Raghava B, Parameshwarappa G, Acharya A, Swaroop TR, Rangappa KS, Ila H. Eur. J. Org. Chem. 2014; 1882
10 Chen CW, Cui SL. J. Org. Chem. 2019; 84: 12157
11 Waldo JP, Larock RC. Org. Lett. 2005; 7: 5203
12 Waldo JP, Larock RC. J. Org. Chem. 2007; 72: 9643
13 Dubrovskiy AV, Larock RC. Org. Lett. 2010; 12: 1180
14 Koufaki M, Fotopoulou T, Kapetanou M, Heropoulos GA, Gonos ES, Chondrogianni N. Eur. J. Med. Chem. 2014; 83: 508
15 Chen HL, Wei D, Zhang JW, Li CL, Yu W, Han B. Org. Lett. 2018; 20: 2906
16 Zhang XW, Hu WL, Chen S, Hu XG. Org. Lett. 2018; 20: 860
17 Yu HF, Yu ZK. Angew. Chem. Int. Ed. 2009; 48: 2929
18 Yu HF, Wang WJ. Synth. Commun. 2020; 50: 1133
19 Zhao YH, Yu HF, Liao PQ, Wang WJ. Chem. Res. Chin. Univ. 2020; 36: 847
20 Wang WJ, Yu HF. Synth. Commun. 2019; 49: 377
21 Hu XY, Yu HF, Wang WJ, Jiang SA, Liu Q, He J. Chin. J. Org. Chem. 2019; 39: 3183
22 Yu HF, Liao PQ, Mei ZM. Synthesis 2020; 52: 2111
23 Yu HF, Li TC, Liao PQ. Synthesis 2012; 44: 3743
24 Yu HF, Liao PQ, Diao QP, Li TC, Xin G, Han LN, Hou DY. Chin. J. Org. Chem. 2014; 34: 1851
25 Yu HF, Li TC, Liao PQ, Diao QP, Xin G, Hou D. Chin. J. Org. Chem. 2014; 34: 956
26 Kashima C, Yoshiwara N, Omote Y. Tetrahedron Lett. 1982; 23: 2955
27 Purkayastha ML, Ila H, Junjappa H. Synthesis 1989; 20
28 Doorenbos NJ, Milewich L. J. Org. Chem. 1966; 31: 3193
29 CCDC 1990800 (3l) and CCDC 1990801 (4l) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via http://www.ccdc.cam.ac.uk/getstructures.

Supplementary Material

Supporting Information