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Review
. 2010 May 26;15(6):3775-815.
doi: 10.3390/molecules15063775.

Thiazolo[3,2-a]benzimidazoles: synthetic strategies, chemical transformations and biological activities

Khalid A Al-Rashood  1 , Hatem A Abdel-Aziz
Affiliations
Review

Thiazolo[3,2-a]benzimidazoles: synthetic strategies, chemical transformations and biological activities

Khalid A Al-Rashood et al. Molecules. .

Abstract

The present review covers the recent synthetic strategies and chemical transformations of thiazolo[3,2-a]benzimidazoles and it also presents the highlights of the biological activities of these compounds.

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Figures

Figure 1
Figure 1
Structure of compounds 1 and 2.
Scheme 1
Scheme 1
Reaction of 2-mercaptobenzimidazole (3) with ketones 4.
Scheme 2
Scheme 2
Cyclization of sulphides 5.
Scheme 3
Scheme 3
Reaction of 2-mercaptobenzimidazole (3) with ketones 9 and 11.
Scheme 4
Scheme 4
Reaction of 2-mercaptobenzimidazoles 3 with α-halo ketones 13.
Scheme 5
Scheme 5
Reaction of 2-mercaptobenzimidazoles (3) with α-halo ketone 17.
Scheme 6
Scheme 6
Reaction of 2-mercaptobenzimidazole (3) with hydrazonyl halides 20.
Scheme 7
Scheme 7
Reaction of 2-mercaptobenzimidazoles 3 with 1,2-dihaloethyl derivatives 24.
Scheme 8
Scheme 8
Reaction of 2-mercaptobenzimidazole (3) with bis-hydrazonoyl chlorides 27.
Scheme 9
Scheme 9
Reaction of 2-mercaptobenzimidazole (3) with 1,2-dibromoethylsulfonyles 30.
Scheme 10
Scheme 10
Reaction of 2-mercaptobenzimidazoles 3 with allyl halides 32.
Scheme 11
Scheme 11
Reaction of 2-mercaptobenzimidazole (3) with propargyl bromide (35).
Scheme 12
Scheme 12
Reaction of 2-mercaptobenzimidazole (3) with bromomalononitrile (39).
Scheme 13
Scheme 13
Reaction of 2-mercaptobenzimidazole (3) with fluoro ethylene derivative 42.
Scheme 14
Scheme 14
Reaction of 2-mercaptobenzimidazole (3) with iodanes 44.
Scheme 15
Scheme 15
Reaction of 2-mercaptobenzimidazole (3) with bromanes 47.
Scheme 16
Scheme 16
Reaction of 2-mercaptobenzimidazole (3) with dimethyl acetylenedicarboxylate (49).
Scheme 17
Scheme 17
Reaction of 2-mercaptobenzimidazole (3) with 1,4-diarylsulfonyl-2-butynes 52.
Scheme 18
Scheme 18
Reaction of 2-mercaptobenzimidazole (3) with arylpropiolates 54.
Scheme 19
Scheme 19
Reaction of 2-mercaptobenzimidazole (3) with epoxyphosphorus derivative 56.
Scheme 20
Scheme 20
Reaction of 2-mercaptobenzimidazole (3) with epoxide derivative 60.
Scheme 21
Scheme 21
Reaction of 2-mercaptobenzimidazole (3) with amidinium salts 64.
Scheme 22
Scheme 22
Reaction of compound 67 with diethyl ether-boron trifluoride 68.
Scheme 23
Scheme 23
Cyclization of compound 70.
Scheme 24
Scheme 24
Reaction of benzimidazole 72 with (chloromethyl)thiirane (73).
Scheme 25
Scheme 25
Reaction of thiazoline-2-thione 76 with methyl iodide.
Figure 2
Figure 2
Chemical Abstract numbering of thiazolo[3,2-a]benzimidazole atoms.
Scheme 26
Scheme 26
Oxidation of 2,3-dihydro-1,1-dioxthiazolo[3,2-a]benzimidazole 81.
Scheme 27
Scheme 27
Reaction of 3-aminothiazolo[3,2-a]-benzimidazole-2-carbonitrile (41) with ketones 4.
Scheme 28
Scheme 28
Reaction of 2-arylidenethiazolo[3,2-a]benzimidazol-3(2H)-one 55 with nitrilimine 83.
Scheme 29
Scheme 29
Reaction of 3-methylthiazolo[3,2-a]benzimidazole (10a) with propiolic esteres 87.
Scheme 30
Scheme 30
Mannich reaction of 3-methylthiazolo[3,2-a]benzimidazole 10a.
Scheme 31
Scheme 31
Reactions of ethanone derivative 10b.
Scheme 32
Scheme 32
Reaction of ethanone 10b with DMF-DMA.
Scheme 33
Scheme 33
Reactions of enaminone 93.
Scheme 34
Scheme 34
Reactions of enaminone 93.
Scheme 35
Scheme 35
Reactions of enaminone 93.
Scheme 36
Scheme 36
Bromination of ethanone 10b.
Scheme 37
Scheme 37
Reaction of ester 15a with acetonitrile.
Scheme 38
Scheme 38
Reaction of ester 15a with hydrazine hydrate.
Scheme 39
Scheme 39
Reactions of hydrazide 137.
Scheme 40
Scheme 40
Reactions of hydrazide 142.
Scheme 41
Scheme 41
Reaction of thiazolone 2 with aromatic aldehydes.
Scheme 42
Scheme 42
Reaction of thiazolone 2 with aldehydes.
Scheme 43
Scheme 43
Reaction of thiazolone 2 with aldehydes.
Scheme 44
Scheme 44
Reaction of thiazolone 2 with aldehydes.
Scheme 45
Scheme 45
One-pot reaction of pyridines 157.
Scheme 46
Scheme 46
Synthesis of spiro-pyrrolidine 161.
Scheme 47
Scheme 47
Coupling reaction of thiazolone 2.
Scheme 48
Scheme 48
Reaction of thiazolone 2 with phenyl isothiocyanate.
Scheme 49
Scheme 49
Reaction of thiazolone 2 with carbon disulphide.
Scheme 50
Scheme 50
Reactions of 3-aminothiazolo[3,2-a]bezimidazole-2-carbonitrile 41.
Scheme 51
Scheme 51
Reactions of 3-aminothiazolo[3,2-a]bezimidazole-2-carbonitrile 41.
Scheme 52
Scheme 52
Reactions of pyrimidinone 173.
Scheme 53
Scheme 53
Reactions of chloro pyrimidine 180.
Scheme 54
Scheme 54
Reactions of hydrazino pyrimidine 184.
Scheme 55
Scheme 55
Reactions of 3-chloromethythiazolo[3,2-a]benzimidazole (196).
Scheme 56
Scheme 56
Reactions of thiazolones 2 with piperazines.
Scheme 57
Scheme 57
Bromination of ethanone 10b and ester 15a.
Scheme 58
Scheme 58
Reaction of compounds 203 with alkyl or aryl halides.
Scheme 59
Scheme 59
Acid hydrolysis of arylidene derivatives 55.
Figure 3
Figure 3
Chemical structure of tilomisole (WY-18,251) and levamisole.
Figure 4
Figure 4
Chemical structure of YM-298198.
Figure 5
Figure 5
6-Aminomethyl-substituted thiazolobenz­imidazole derivatives.
See this image and copyright information in PMC

References

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    1. Kochergin P.M., Krasovskii A.N. Synthesis of thiazolo[3,2-a]benzimidazole. Khimiya Geterotsiklicheskikh Soedinenii. 1966;6:945–946.
    1. Alper A.E., Taurins A. Thiazolo[3,2-a]benzimidazoles. Can. J. Chem. 1967;45:2903–2912. doi: 10.1139/v67-471. - DOI
    1. Andersag H., Westphal K. Über die synthese des antineuritischen vitamins. Ber. Deut. Chem. Ges. 1937;70:2035–2054. doi: 10.1002/cber.19370701002. - DOI
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