Condensed Benzimidazoles of Type 6‐5‐6

Tennant, G.

doi:10.1002/9780470187166.ch2

Chemistry of Heterocyclic Compounds: A Series of Monographs

1981

DOI: 10.1002/9780470187166.ch2

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Condensed Benzimidazoles of Type 6‐5‐6

G. Tennant¹

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2003

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Heteroaromatic Annulation of 2-Methyl/2-Cyanomethylbenzimidazole Dianions withα-Oxoketene Dithioacetals: A Highly Regioselective Synthetic Protocol for 1,2- and 2,3-Substituted/Annulated Pyrido[1,2-a]benzimidazoles

et al. 2003

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A highly efficient and regioselective annulation protocol for a series of linearly 2,3- and angularly 1,2-substituted and annulated pyrido[1,2-a]benzimidazoles involving [3 + 3] cyclocondensation of the dianions generated from 2-methyl (2A) and 2-cyanomethyl (3A) benzimidazoles with a variety of alpha-oxoketene dithioacetals has been reported. Thus the dianion 2A derived from 2-methylbenzimidazole has been shown to undergo regioselective 1,2-addition with various alpha-oxoketene dithioacetals derived from acyclic (4a-d) and cyclic ketones (13a,b, 20, 29 and 32) to afford various carbinol acetals which on intramolecular cyclocondensation in the presence of phosphoric acid furnish the corresponding 1-methylthio-2,3-substituted (5a-c) and 2,3-fused linear polycyclic (14a,b,21, 30, and 33) pyrido[1,2-a]benzimidazoles in high yields. Similarly the dianion 3A from 2-cyanomethylbenzimidazole undergoes one-pot conjugate addition-elimination and cyclocondensation with these alpha-oxoketene dithioacetals to give 4-cyano-3-(methylthio)-1(or 1,2-)-substituted (6a-d) and the corresponding angularly 1,2-fused (16a,b, 23, 31, and 34) polycylic analogues of pyrido[1,2-a]benzimidazoles in excellent yields.

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Heteroaromatic Annulation of 2-Methyl/2-Cyanomethylbenzimidazole Dianions withα-Oxoketene Dithioacetals: A Highly Regioselective Synthetic Protocol for 1,2- and 2,3-Substituted/Annulated Pyrido[1,2-a]benzimidazoles

et al. 2003

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Condensed Benzimidazoles of Type 6‐5‐6

Cited by 1 publication

References 80 publications

Heteroaromatic Annulation of 2-Methyl/2-Cyanomethylbenzimidazole Dianions withα-Oxoketene Dithioacetals: A Highly Regioselective Synthetic Protocol for 1,2- and 2,3-Substituted/Annulated Pyrido[1,2-a]benzimidazoles

Heteroaromatic Annulation of 2-Methyl/2-Cyanomethylbenzimidazole Dianions withα-Oxoketene Dithioacetals: A Highly Regioselective Synthetic Protocol for 1,2- and 2,3-Substituted/Annulated Pyrido[1,2-a]benzimidazoles

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