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Synthesis
DOI: 10.1055/a-2315-1934
DOI: 10.1055/a-2315-1934
paper
Photocatalytic Annulation of Enaminones with Thioureas for the Synthesis of 2-Aminothiazoles via Tandem C–S and C–N Bond Formation
The authors thank the National Natural Science Foundation of China (Grant: 22161022) for funding.
Abstract
Visible-light photocatalytic reactions between enaminones and thioureas leading to thiazole products have been achieved. The annulation process consists of tandem C–S and C–N bond formation by running reactions under air atmosphere at ambient temperature. Broad substrate tolerance of the sustainable protocol has been verified by the practical synthesis of divergent thiazoles with both monocyclic and fused cyclic structures.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2315-1934.
- Supporting Information
Publication History
Received: 01 April 2024
Accepted after revision: 26 April 2024
Accepted Manuscript online:
26 April 2024
Article published online:
15 May 2024
© 2024. Thieme. All rights reserved
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References
-
1a
Ayati A,
Emami S,
Asadipour A,
Shafiee A,
Foroumadi A.
Eur. J. Med. Chem. 2015; 97: 699
-
1b
Gümüş M,
Yakan M,
Koca İ.
Future Med. Chem. 2019; 11: 1979
-
1c
Ji M,
Dong C,
Guo Q,
Du M,
Guo Q,
Sun X,
Wang E,
Zhou E.
Macromol. Rapid Commun. 2023; 44: 2300102
-
1d
Narasimhamurthy KH,
Sajith AM,
Joy MN,
Rangappa KS.
ChemistrySelect 2020; 5: 5629
-
1e
Li M,
Xia D,
Wang Y,
Cheng X,
Gong J,
Chen Y,
Lü X.
Chin. J. Org. Chem. 2023; 43: 686
-
1f
Homer A,
Seitz O.
Synthesis 2023; 55: 3251
-
1g
Chen S,
Shao Y,
Fu X,
Chen Q,
Du X,
Tan C.
Chin. J. Org. Chem. 2022; 42: 3870
-
2
Hantzsch A,
Weber JH.
Ber. Dtsch. Chem. Ges. 1887; 20: 3118
-
3
Hassell-Hart S,
Speranzini E,
Srikwanjai S,
Hossack E,
Roe SM,
Fearon D,
Akinobsede D,
Hare S,
Spencer J.
Org. Lett. 2022; 24: 7924
-
4a
Banerjee R,
Ali D,
Mondal N,
Choudhury LH.
J. Org. Chem. 2024; 89: 4423
-
4b
Dai T,
Cui C,
Qi X,
Cheng Y,
He Q,
Zhang X,
Luo X,
Yang C.
Org. Biomol. Chem. 2020; 18: 6162
-
4c
Zhao P,
Zhou Y,
Wang C,
Wu A.-X.
J. Org. Chem. 2024; 89: 2505-2515
-
5a
Sharma A,
Gola AK,
Pandey SK.
Chem. Commun. 2023; 59: 10247
-
5b
Tang X,
Yang J,
Zhu Z,
Zheng M,
Wu W,
Jiang H.
J. Org. Chem. 2016; 81: 11461
-
5c
Banert K,
Al-Hourani BJ,
Groth S,
Vrobel K.
Synthesis 2005; 2920
-
5d
Chen K,
Zhao B,
Liu Y,
Wan J.-P.
J. Org. Chem. 2022; 87: 14957
-
5e
Liu Y,
Zhang T,
Wan J.-P.
J. Org. Chem. 2022; 87: 8248
-
6a
Wang X,
Qiu X,
Wei J,
Liu J,
Song S,
Wang W,
Jiao N.
Org. Lett. 2018; 20: 2632
-
6b
Huang H,
Xu Z,
Ji X,
Li B,
Deng G.-J.
Org. Lett. 2018; 16: 4917
-
6c
Ma X,
Yu X,
Hang H,
Zhou Y,
Song Q.
Org. Lett. 2020; 22: 5284
-
6d
Chen L,
Xuchen X,
Wang F,
Yang Y,
Deng G,
Liu Y,
Liang Y.
Org. Biomol. Chem. 2021; 19: 10068
-
6e
Jiang J,
Huang H,
Deng G.
Green Chem. 2019; 21: 986
-
7a
Singh KR,
Santhosh C,
Swaroop TR,
Sadashiva MP.
Org. Biomol. Chem. 2022; 20: 5771
-
7b
Guan Z.-R,
Liu Z.-M,
Wan Q,
Ding M.-W.
Tetrahedron 2020; 76: 131101
-
7c
Hori M,
Nogi K,
Nagaki A,
Yorimitsu H.
Asian J. Org. Chem. 2019; 8: 1084
-
8a
Li D,
Chen L,
Jin Y,
Wang X,
Liu L,
Li Y,
Chen G,
Wu G,
Qin Y,
Yang L,
Wang M,
Zhao L,
Xu Z,
Wen J.
Green Chem. 2023; 25: 4656
-
8b
Guo H,
Liu Y,
Wen C,
Wan J.-P.
Green Chem. 2022; 24: 5058
-
8c
Fu R,
Wang Y,
Xia F,
Zhang H,
Sun Y,
Yang D,
Wang Y,
Yin P.
J. Org. Chem. 2019; 84: 12237
-
9a
Pitre SP,
Overman LE.
Chem. Rev. 2022; 122: 1717
-
9b
Han Y,
Zhou L,
Wang C,
Feng S,
Ma R,
Wan J.-P.
Chin. Chem. Lett. 2024; 35: 108977
-
9c
Yin C,
Wang M,
Cai Z,
Yuan B,
Hu P.
Synthesis 2022; 54: 4864
-
9d
Sun K,
Lv Q.-Y,
Chen X.-L,
Qu L.-B,
Yu B.
Green Chem. 2021; 23: 232
-
9e
Zhang Q.-B,
Yang Y,
Zhang S,
Liu Q.
Adv. Synth. Catal. 2023; 365: 3556
-
9f
Gao P.-P,
Xiao W.-J,
Chen J.-R.
Chin. J. Org. Chem. 2022; 42: 3923
-
9g
Xu H,
Zhang J,
Zuo J,
Wang F,
Lü J,
Hun X,
Yang D.
Chin. J. Org. Chem. 2022; 42: 4037
-
10
Chen Z,
Xue F,
Zhang Y,
Jin W,
Wang B,
Xia Y,
Xie M,
Abdukader A,
Liu C.
Org. Lett. 2022; 24: 3149
-
11
Huang X,
Chen H,
Huang Z,
Xu Y,
Li F,
Ma X,
Chen Y.
J. Org. Chem. 2019; 84: 15283
-
12
Zeng J,
Wan J.-P,
Liu Y.
J. Org. Chem. 2022; 87: 13195
-
13a
Han Y,
Zhou L,
Wang C,
Feng S,
Ma R,
Wan J.-P.
Chin. Chem. Lett. 2024; 35: 108977
-
13b
Fu L,
Wan J.-P.
Tetrahedron Lett. 2023; 130: 154766
-
13c
Wang Z,
Zhao B,
Liu Y,
Wan J.-P.
Adv. Synth. Catal. 2022; 364: 1508
-
13d
Huang J,
Yu F.
Synthesis 2021; 53: 587
-
13e
Xia X.-F,
Niu Y.-N.
Org. Biomol. Chem. 2022; 20: 282
-
13f
Liu N,
Cuan X,
Li H,
Duan X.
Chin. J. Org. Chem. 2023; 43: 602
-
13g
Wu H,
Luo T,
Wan J.-P,
Jiang J,
Liu Y.
Eur. J. Org. Chem. 2022; e202200552
-
13h
Xu X.-H,
Wen J.-H,
Chen Y,
Dong Z.-B.
Adv. Synth. Catal. 2024; 366: 1649
-
13i
Xu X.-H,
Dong Z.
Org. Biomol. Chem. 2022; 20: 8533
-
14a
Liu Y,
Deng L,
Guo H,
Wan J.-P.
Org. Lett. 2024; 26: 46
-
14b
Yavari I,
Hassaini Z,
Sabbaghan M.
Tetrahedron Lett. 2008; 49: 844
-
15a
Ye J,
Liu Y,
Luo J,
Wan J.-P.
Org. Lett. 2023; 25: 8451
-
15b
Gayon E,
Szmczyk M,
Gérard H,
Vrancken E,
Campagne J.-M.
J. Org. Chem. 2012; 77: 9205
-
15c
Wang Z.-W,
Zheng Y,
Qian Y.-E,
Guan J.-P,
Lu W.-D,
Yuan C.-P,
Xiao J.-A,
Chen K,
Xiang H.-Y,
Yang H.
J. Org. Chem. 2022; 87: 1477
-
16a
Gao H,
Zhou L,
Wan J.-P,
Liu Y.
J. Org. Chem. 2023; 88: 7188
-
16b
Cheng G,
Weng Y,
Yang X,
Cui X.
Org. Lett. 2015; 17: 3790
-
16c
Bodala V,
Podugu RL,
Yettula K,
Gollamudi PO,
Vidavalur S,
Pulipaka S.
Chem. Asian J. 2023; 18: e202201004
-
17a
Zhong Z,
Liao L,
Liu Y,
Zhang M,
Wan J.-P.
Chem. Commun. 2023; 59: 6885
-
17b
Li W,
Dong Z,
Zhang Y,
Zeng Z,
Usman M,
Liu W.-B.
J. Org. Chem. 2019; 84: 7995
-
17c
Jillella R,
Raju S,
Hsiao H.-C,
Hsu D.-S,
Chuang S.-C.
Org. Lett. 2020; 22: 6252
-
17d
Tang S,
Gao X,
Lei A.
Chem. Commun. 2017; 53: 3354
-
18a
Song W,
Liu Y,
Yan N,
Wan J.-P.
Org. Lett. 2023; 25: 2139
-
18b
Zheng Y,
Yang C,
Zhang-Negrerie D,
Du Y,
Zhao K.
Tetrahedron Lett. 2013; 54: 6157
-
19
Tian S,
Liu Y,
Wan C,
Wan J.-P,
Hao G.
J. Org. Chem. 2023; 88: 2433
-
20a
Fu L,
Wan J.-P,
Zhou L,
Liu Y.
Chem. Commun. 2022; 58: 1808
-
20b
Yang J,
Zhou P,
Hu B,
Zhao S,
Zhang Q,
Xu L,
Yang R,
Yu F.
ChemistrySelect 2018; 3: 11938
-
20c
Dattatri,
Singam MK. R,
Nanubolu JB,
Reddy MS.
Org. Biomol. Chem. 2022; 20: 6363
-
20d
Zhao Y,
Fan Y,
Meng X,
Kang X,
Ji Z,
Yan S,
Tian L.
J. Org. Chem. 2022; 87: 11131
-
20e
González-Soria MJ,
Alonso F.
Adv. Synth. Catal. 2019; 361: 5005
-
21a
Guo H,
Tian L,
Liu Y,
Wan J.-P.
Org. Lett. 2022; 24: 228
-
21b
Zhang Q,
Hu B,
Zhao Y,
Zhao S,
Wang Y,
Zhang B,
Yan S,
Yu B.
Eur. J. Org. Chem. 2020; 1154
-
21c
Feng J,
Wang Y,
Gao L,
Yu Y,
Baell JB,
Huang F.
J. Org. Chem. 2022; 87: 13138
-
21d
Guo H,
Liu Y,
Wan J.-P.
Green Synth. Catal. 2024; in press DOI: 10.1016/j.gresc.2023.10.004.
-
22a
Huo J,
Geng X,
Li W,
Zhang P,
Wang L.
Adv. Synth. Catal. 2022; 364: 3539
-
22b
Rahul P,
Veena S,
Jubi J.
J. Org. Chem. 2022; 87: 13708
-
22c
Zhou P,
Hu B,
Wang Y,
Zhang Q,
Li X,
Yan S,
Yu F.
Eur. J. Org. Chem. 2018; 4527