单质硫: 合成含硫杂环的优质硫源

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Sulfur-containing heterocyclic compounds are widely applied in many areas such as drugs, molecular devices and materials, etc ., so their synthesis methods have attracted much attention. The key step for the synthesis of sulfur-containing heterocycles is the construction of C—S bond, which is generally realized by C—H bond functionalization or C—X bond coupling reaction with sulfur-containing organic or inorganic substances. Elemental sulfur is cheap, available and stable, and it is an excellent sulfur atom donor for the synthesis of sulfur-containing heterocycles. Therefore, the synthesis of sulfur-containing heterocycles from elemental sulfur has become a research hotspot. Herein, the recent research progress of synthesis of sulfur-containing heterocyclic employing sulfur as sulfur-source is reviewed.

Key words: sulfur-containing heterocycle, elemental sulfur, C—S bond construction, multi-component cascade reaction

肖立伟, 刘光仙, 任萍, 吴彤桐, 卢玉伟, 孔洁. 单质硫: 合成含硫杂环的优质硫源[J]. 有机化学 , 2022, 42(4): 1002-1012.

Liwei Xiao, Guangxian Liu, Ping Ren, Tongtong Wu, Yuwei Lu, Jie Kong. Elemental Sulfur: An Excellent Sulfur-Source for Synthesis of Sulfur-Containing Heterocyclics[J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1002-1012.

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Entry	R ² -FG	Product	Cat./base	Reaction condition	Yield/%	Ref.
1	Aldehyde	2-Arylbenzothiazole	CuCl ₂ -Phen/K ₂ CO ₃	H ₂ O, 100 ℃	52~96	[ 7 ]
2	Benzylchloride	2-Arylbenzothiazole	Cu(OAc) _2/ Na ₂ CO ₃	DMSO, 130 ℃	53~98	[ 8 ]
3	Benzylamine	2-Arylbenzothiazole	Cu(OAc) ₂ /DABCO	DMSO, 100 ℃	10~90	[ 9 ]
4	Benzylamine	2-Arylbenzothiazole	CuCl-Phen	H ₂ O, 100 ℃	60~88	[ 10 ]
5	Terminalalkyne	2-Benzylbenzothiazole	CuTC/DBU	MeCN/H ₂ O, 130 ℃	45~84	[ 11 ]
6	Terminalalkyne	2-Arylbenzothiazole	CuI-Phen/K ₂ CO ₃	DMSO, 110 ℃	62~90	[ 11 ]
7	N -Tosylhydrazone	2-Arylbenzothiazole	CuSCN/DBU	DMSO, 110 ℃	63~84	[ 12 ]
8	N -Tosylhydrazone	2-Benzylbenzothiazole	CuI, CsF/DABCO	MeCN, 130 ℃	57~70	[ 12 ]
9	Quaternaryammonium	2-Alkylbenzothiazole	KOH	H ₂ O, 140 ℃	74~95	[ 13 ]

Entry	R ² -FG	Product	Cat./base	Reaction condition	Yield/%	Ref.
1	Aldehyde	2-Arylbenzothiazole	CuCl ₂ -Phen/K ₂ CO ₃	H ₂ O, 100 ℃	52~96	[ 7 ]
2	Benzylchloride	2-Arylbenzothiazole	Cu(OAc) _2/ Na ₂ CO ₃	DMSO, 130 ℃	53~98	[ 8 ]
3	Benzylamine	2-Arylbenzothiazole	Cu(OAc) ₂ /DABCO	DMSO, 100 ℃	10~90	[ 9 ]
4	Benzylamine	2-Arylbenzothiazole	CuCl-Phen	H ₂ O, 100 ℃	60~88	[ 10 ]
5	Terminalalkyne	2-Benzylbenzothiazole	CuTC/DBU	MeCN/H ₂ O, 130 ℃	45~84	[ 11 ]
6	Terminalalkyne	2-Arylbenzothiazole	CuI-Phen/K ₂ CO ₃	DMSO, 110 ℃	62~90	[ 11 ]
7	N -Tosylhydrazone	2-Arylbenzothiazole	CuSCN/DBU	DMSO, 110 ℃	63~84	[ 12 ]
8	N -Tosylhydrazone	2-Benzylbenzothiazole	CuI, CsF/DABCO	MeCN, 130 ℃	57~70	[ 12 ]
9	Quaternaryammonium	2-Alkylbenzothiazole	KOH	H ₂ O, 140 ℃	74~95	[ 13 ]

2-卤代苯胺和硫为原料合成2-取代苯并噻唑a Table 1. Synthesis of 2-substituted benzothiazole from 2-haloaniline and sulfur

Entry	Ar-FG	Product	Cat.	Reaction condition	Yield/%	Ref.
1	Methylaromatic	2-Arylbenzothiazole	—	275 ℃	15~74	[ 14 ]
2	Methylaromatic	2-Arylnaphthothiazole	—	275 ℃	41~50	[ 14 ]
3	2-Methylarene	2-Heteroarylbenzothiazole	NH ₄ I	NMP, air, 160 ℃	37~87	[ 15 ]
4	Arylaldehyde	2-Arylnaphtho[2,1- d ]thiazole	NH ₄ I/4 Å MS	DMSO/PhCl, 140 ℃	61~98	[ 16 ]
5	Arylaldehyde	2-Arylbenzothiazole	KI	O ₂ , NMP, 150 ℃	40~79	[ 16 ]
6	Styrene	2-Benzylbenzothiazole	NH ₄ I	NMP, air, 140 ℃	63~88	[ 17 ]
7	Arylacetylene	2-Benzylbenzothiazole	NH ₄ I	NMP, air, 140 ℃	57~81	[ 17 ]
8	Ether	2-Aryl, alkylbenzothiazole	TBHP ^b /KI	DMSO, air, 130 ℃	41~81	[ 18 ]
9	Aliphaticamine	2-Aryl, alkylbenzothiazole	sealed tube	DMSO, 140 ℃	42~90	[ 19 ]
10	Acetophenone	2-Arylbenzothiazole	I ₂ , TBAI ^c	DMSO/PhCl, 140 ℃	40~81	[ 20 ]
11	Acetophenone	2-Aroylbenzothiazole	I ₂ ,	DMSO/PhCl, 140 ℃	42~78	[ 21 ]
12	Isatin	2-(2'-Aminophenyl)benzothiaole	KI/4 Å MS	DMSO, 120 ℃	60~85	[ 22 ]

Entry	Ar-FG	Product	Cat.	Reaction condition	Yield/%	Ref.
1	Methylaromatic	2-Arylbenzothiazole	—	275 ℃	15~74	[ 14 ]
2	Methylaromatic	2-Arylnaphthothiazole	—	275 ℃	41~50	[ 14 ]
3	2-Methylarene	2-Heteroarylbenzothiazole	NH ₄ I	NMP, air, 160 ℃	37~87	[ 15 ]
4	Arylaldehyde	2-Arylnaphtho[2,1- d ]thiazole	NH ₄ I/4 Å MS	DMSO/PhCl, 140 ℃	61~98	[ 16 ]
5	Arylaldehyde	2-Arylbenzothiazole	KI	O ₂ , NMP, 150 ℃	40~79	[ 16 ]
6	Styrene	2-Benzylbenzothiazole	NH ₄ I	NMP, air, 140 ℃	63~88	[ 17 ]
7	Arylacetylene	2-Benzylbenzothiazole	NH ₄ I	NMP, air, 140 ℃	57~81	[ 17 ]
8	Ether	2-Aryl, alkylbenzothiazole	TBHP ^b /KI	DMSO, air, 130 ℃	41~81	[ 18 ]
9	Aliphaticamine	2-Aryl, alkylbenzothiazole	sealed tube	DMSO, 140 ℃	42~90	[ 19 ]
10	Acetophenone	2-Arylbenzothiazole	I ₂ , TBAI ^c	DMSO/PhCl, 140 ℃	40~81	[ 20 ]
11	Acetophenone	2-Aroylbenzothiazole	I ₂ ,	DMSO/PhCl, 140 ℃	42~78	[ 21 ]
12	Isatin	2-(2'-Aminophenyl)benzothiaole	KI/4 Å MS	DMSO, 120 ℃	60~85	[ 22 ]

苯胺/萘胺和硫为原料合成2-取代苯并噻唑a Table 2. Synthese of 2-substituted benzothiazoles from anilines/naphthylamine and sulfur

Entry	Ar-FG	Product	Cat./base	Reaction condition	Yield%	Ref.
1	Methylhetarene	2-Hetarylbenzothiazole	—	120 ℃	37~85	[ 25 ]
2	Methylhetarene	2-Hetarylbenzothiazole	NH ₄ I	Sulfolane, 175 ℃	9~60	[ 26 ]
3	Benzaldehyde	2-Arylbenzothiazole	NMM	130 ℃	60~80	[ 27 ]
4	Benzylamine	2-Arylbenzothiazole	Pyridine	100 ℃	61~80	[ 28 ]
5	Aliphatic amine	2-Arylbenzothiazole	—	130 ℃	52~80	[ 29 ]
6	Acetophenone	2-Aroylbenzothiazole	NMM	120 ℃	52~92	[ 30 ]
7	Arylacetic acid	2-Arylbenzothiazole	NMM	110 ℃	46~75	[ 31 ]
8	Benzylic alcohol	2-Arylbenzothiazole	FeCl ₃ /KHCO ₃ /NH ₄ I	NMP, 160 ℃	25~80	[ 32 ]

Entry	Ar-FG	Product	Cat./base	Reaction condition	Yield%	Ref.
1	Methylhetarene	2-Hetarylbenzothiazole	—	120 ℃	37~85	[ 25 ]
2	Methylhetarene	2-Hetarylbenzothiazole	NH ₄ I	Sulfolane, 175 ℃	9~60	[ 26 ]
3	Benzaldehyde	2-Arylbenzothiazole	NMM	130 ℃	60~80	[ 27 ]
4	Benzylamine	2-Arylbenzothiazole	Pyridine	100 ℃	61~80	[ 28 ]
5	Aliphatic amine	2-Arylbenzothiazole	—	130 ℃	52~80	[ 29 ]
6	Acetophenone	2-Aroylbenzothiazole	NMM	120 ℃	52~92	[ 30 ]
7	Arylacetic acid	2-Arylbenzothiazole	NMM	110 ℃	46~75	[ 31 ]
8	Benzylic alcohol	2-Arylbenzothiazole	FeCl ₃ /KHCO ₃ /NH ₄ I	NMP, 160 ℃	25~80	[ 32 ]

硝基苯和硫为原料合成2-取代苯并噻唑a Table 3. Synthese of 2-substituted benzothiazoles from nitrobenzenes and sulfur

Entry	Ar ² -FG	Product	Cat./base	Reaction condition	Yield/%	Ref..
1	Arylmethylbromide	3,5-Diaryl-1,2,4-thiadiazole	LiO ^t Bu	Toluene, 140 ℃	45~67	[ 39 ]
2	Methylketone	3-Aryl-5-acyl-1,2,4-thiadiazole	PaCl ₂ /K ₂ HPO ₄	DMSO, 130 ℃	35~75	[ 40 ]
3	2-Methylquinoline	3,5-Diaryl-1,2,4-thiadiazole	K ₃ PO ₄	DMSO, 120 ℃	42~93	[ 41 ]
4	Aromaticaldehyde	3,5-Diaryl-1,2,4-thiadiazole	K ₃ PO ₄	DMSO, 120 ℃	48~63	[ 41 ]

Entry	Ar ² -FG	Product	Cat./base	Reaction condition	Yield/%	Ref..
1	Arylmethylbromide	3,5-Diaryl-1,2,4-thiadiazole	LiO ^t Bu	Toluene, 140 ℃	45~67	[ 39 ]
2	Methylketone	3-Aryl-5-acyl-1,2,4-thiadiazole	PaCl ₂ /K ₂ HPO ₄	DMSO, 130 ℃	35~75	[ 40 ]
3	2-Methylquinoline	3,5-Diaryl-1,2,4-thiadiazole	K ₃ PO ₄	DMSO, 120 ℃	42~93	[ 41 ]
4	Aromaticaldehyde	3,5-Diaryl-1,2,4-thiadiazole	K ₃ PO ₄	DMSO, 120 ℃	48~63	[ 41 ]

芳基脒和硫为原料合成多取代1,2,4-噻二唑 Table 4. Synthesis of polysubstituted 1,2,4-thiadiazoles from arylamidines and sulfur

Entry	Substrate 1	Substrate 2	Cat./base	Reaction condition	Yield/%	Ref.
1	Ketone	Cyanoacetone	Piperidine	EtOH, 55~65 ℃	8~86	[ 46 ]
2	Ketone, aldehyde	Dicyanomethane	Imidazole	DMF, 60 ℃, N ₂	27~88	[ 47 ]
3	Ketone, aldehyde	Cyanomethylene	Morpholine	PEG-600, U.S.	29~98	[ 48 ]
4	Cycloketone	Ethylcyanoacetate	Morpholine	M.W., 120 ℃	22~87	[ 49 ]
5	Ketone, aldehyde	Malononitrile	ZnO	100 ℃	37~86	[ 50 ]
6	Ketone	Malononitrile	NaAlO ₂	EtOH, 60 ℃	26~97	[ 51 ]
7	Arylacetaldehyde	1,3-Diketone	K ₂ CO ₃ /KHCO ₃	DMSO, 95 ℃	36~84	[ 52 ]
8	Chalcone	Arylacetonitrile	DBU	DMSO/DABCO, 80 ℃	43~75	[ 53 ]
9	Arylmethylketone	Arylmethylketone	Anline/ p -TsA	120 ℃, Ar	48~88	[ 54 ]

Entry	Substrate 1	Substrate 2	Cat./base	Reaction condition	Yield/%	Ref.
1	Ketone	Cyanoacetone	Piperidine	EtOH, 55~65 ℃	8~86	[ 46 ]
2	Ketone, aldehyde	Dicyanomethane	Imidazole	DMF, 60 ℃, N ₂	27~88	[ 47 ]
3	Ketone, aldehyde	Cyanomethylene	Morpholine	PEG-600, U.S.	29~98	[ 48 ]
4	Cycloketone	Ethylcyanoacetate	Morpholine	M.W., 120 ℃	22~87	[ 49 ]
5	Ketone, aldehyde	Malononitrile	ZnO	100 ℃	37~86	[ 50 ]
6	Ketone	Malononitrile	NaAlO ₂	EtOH, 60 ℃	26~97	[ 51 ]
7	Arylacetaldehyde	1,3-Diketone	K ₂ CO ₃ /KHCO ₃	DMSO, 95 ℃	36~84	[ 52 ]
8	Chalcone	Arylacetonitrile	DBU	DMSO/DABCO, 80 ℃	43~75	[ 53 ]
9	Arylmethylketone	Arylmethylketone	Anline/ p -TsA	120 ℃, Ar	48~88	[ 54 ]

通过Gewald反应合成多取代2-氨基噻吩 Table 5. Synthesis of multisubstituted 2-aminothiophenes via Gewald reaction

Entry	R ² -FG	Product	Cat./base	Reaction condition	Yield%	Ref.
1	Arylaldehyde	2-Arylbenzothienothiazole	CuBr/Li ₂ CO ₃	DMSO, 120 ℃	48~91	[ 67 ]
2	Arylacetylene	2-Arylbenzothienothiazole ^b	CuOTf/TBD	DMSO/hexane, 120 ℃	44~83	[ 68 ]
3	Arylaldehyde	2-Arylbenzothienothiazole ^b	CuCl/TBD	DMSO/hexane, 120 ℃	41~90	[ 68 ]
4	Methyl- N -heteroarene	2-Arylbenzothienothiazole	Cs ₂ CO ₃	DMSO, 120 ℃	22~62	[ 69 ]
5	Arylacetic acid or ester	2-Arylbenzothienothiazole	Li ₂ CO ₃	DMSO, 120 ℃	65~92	[ 70 ]
6	Isothiocyanate	2-Aminobenzothienothiazole	KSCN/Li ₂ CO ₃	DMSO, 120 ℃	32~82	[ 71 ]
7	Acetophenone	2-Aroylthienothiazole	TBD	DMSO, 120 ℃	31~87	[ 72 ]

Entry	R ² -FG	Product	Cat./base	Reaction condition	Yield%	Ref.
1	Arylaldehyde	2-Arylbenzothienothiazole	CuBr/Li ₂ CO ₃	DMSO, 120 ℃	48~91	[ 67 ]
2	Arylacetylene	2-Arylbenzothienothiazole ^b	CuOTf/TBD	DMSO/hexane, 120 ℃	44~83	[ 68 ]
3	Arylaldehyde	2-Arylbenzothienothiazole ^b	CuCl/TBD	DMSO/hexane, 120 ℃	41~90	[ 68 ]
4	Methyl- N -heteroarene	2-Arylbenzothienothiazole	Cs ₂ CO ₃	DMSO, 120 ℃	22~62	[ 69 ]
5	Arylacetic acid or ester	2-Arylbenzothienothiazole	Li ₂ CO ₃	DMSO, 120 ℃	65~92	[ 70 ]
6	Isothiocyanate	2-Aminobenzothienothiazole	KSCN/Li ₂ CO ₃	DMSO, 120 ℃	32~82	[ 71 ]
7	Acetophenone	2-Aroylthienothiazole	TBD	DMSO, 120 ℃	31~87	[ 72 ]

酮肟酸(酯)为原料合成苯并噻吩并噻唑a Table 6. Synthese of benzo[4,5]thieno[3,2-d]thiazole from oxime esters

Entry	R ² -FG	Product	Cat./acid	Reaction condition	Yield%	Ref.
1	Alkyne	Thieno[2,3- b ]indole	HCl	DMF, 150 ℃	31~82	[ 77 ]
2	Alkene	Thieno[2,3- b ]indole	HCl/HOAc	DMF, 150 ℃	30~78	[ 77 ]
4	Acetophenone	3-Aryl thieno[2,3- b ]indole	HI/phenylalanine	CF ₃ Ph/dioxane, 130 ℃	28~71	[ 78 ]
5	Acetophenone	2-Aryl thieno[2,3- b ]indole	HOAc	DMF, 150 ℃	37~84	[ 78 ]
3	Cyclohexanone	Benzothieno[2,3- b ]indole	PdI ₂ /CPDO ^a	o -Cl ₂ C ₆ H ₄ , 125 ℃	38~72	[ 79 ]
6	Cyclohexanone	Benzothieno[2,3- b ]indole	I ₂	NMP ^c , 150 ℃	28~83	[ 80 ]
7	Cyclohexanone	3-Arylindole	BF ₃ /DPE ^b	DMF, 150 ℃	33~89	[ 80 ]
8	Cyclohexanone	3-Arylindole	IBr	DPE/DMA ^d , 150 ℃	60~93	[ 80 ]

Entry	R ² -FG	Product	Cat./acid	Reaction condition	Yield%	Ref.
1	Alkyne	Thieno[2,3- b ]indole	HCl	DMF, 150 ℃	31~82	[ 77 ]
2	Alkene	Thieno[2,3- b ]indole	HCl/HOAc	DMF, 150 ℃	30~78	[ 77 ]
4	Acetophenone	3-Aryl thieno[2,3- b ]indole	HI/phenylalanine	CF ₃ Ph/dioxane, 130 ℃	28~71	[ 78 ]
5	Acetophenone	2-Aryl thieno[2,3- b ]indole	HOAc	DMF, 150 ℃	37~84	[ 78 ]
3	Cyclohexanone	Benzothieno[2,3- b ]indole	PdI ₂ /CPDO ^a	o -Cl ₂ C ₆ H ₄ , 125 ℃	38~72	[ 79 ]
6	Cyclohexanone	Benzothieno[2,3- b ]indole	I ₂	NMP ^c , 150 ℃	28~83	[ 80 ]
7	Cyclohexanone	3-Arylindole	BF ₃ /DPE ^b	DMF, 150 ℃	33~89	[ 80 ]
8	Cyclohexanone	3-Arylindole	IBr	DPE/DMA ^d , 150 ℃	60~93	[ 80 ]

吲哚为原料合成噻吩并[2,3-b]吲哚 Table 7. Synthesis of thieno[2,3-b]indoles from indoles

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