One-Pot Synthesis of 2,3-Dihydro-1<i>H</i>-benzimidazoles

Plaskon, Andrey S.; Volochnyuk, Dmitriy M.; Shivanyuk, Alexander; Tolmachev, Andrey A.

doi:10.1021/jo0712087

Cited by 28 publications

(13 citation statements)

References 14 publications

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“…When imines are employed in the role of hydride acceptors, two reaction modes become accessible, namely the exo ‐1,5‐hydride‐shift/cyclization (Scheme a, b) and endo ‐1,6‐hydride‐shift/cyclization processes (Scheme c) 16–18. The first of these reaction classes affords six‐membered aminals as products ( 24 and 26 ).…”

Section: Co and Cn Bonds As Hydride Acceptorsmentioning

confidence: 99%

“…Recently, Seidel and co‐workers introduced the use of catalytic amounts of acid to promote both imine formation and hydride‐shift/cyclization reactions in a one‐pot fashion (Scheme b) 17. The other (abnormal) subset of these reactions involves an unusual endo ‐1,6‐hydride shift to provide five‐membered aminal products (Scheme c) 18…”

Section: Co and Cn Bonds As Hydride Acceptorsmentioning

confidence: 99%

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The Redox‐Neutral Approach to CH Functionalization

Peng

Maulide

2013

Chemistry A European J

289

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The direct functionalization of C-H bonds is an attractive strategy in organic synthesis. Although several advances have been made in this area, the selective activation of inert sp(3) C-H bonds remains a daunting challenge. Recently, a new type of sp(3) C-H activation mode through internal hydride transfer has demonstrated the potential to activate remote sp(3) C-H linkages in an atom-economic manner. This Minireview attempts to classify recent advances in this area including the transition to non-activated sp(3) C-H bonds and asymmetric hydride transfers.

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Section: Co and Cn Bonds As Hydride Acceptorsmentioning

confidence: 99%

Section: Co and Cn Bonds As Hydride Acceptorsmentioning

confidence: 99%

The Redox‐Neutral Approach to CH Functionalization

Peng

Maulide

2013

Chemistry A European J

289

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“…On the other hand, ureas/thioureas were known to be readily activated by TMSCl to give intermediate 10 [38–39]. Intermediate 10 consequently condenses with the aldehyde which was activated by p -TSA to generate imine 7 .…”

Section: Resultsmentioning

confidence: 99%

Secondary amine-initiated three-component synthesis of 3,4-dihydropyrimidinones and thiones involving alkynes, aldehydes and thiourea/urea

Wan¹,

Lin²,

Hu³

et al. 2014

Beilstein J. Org. Chem.

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SummaryThe three-component reactions of aldehydes, electron deficient alkynes and ureas/thioureas have been smoothly performed to yield a class of unprecedented 3,4-dihydropyrimidinones and thiones (DHPMs). The reactions are initiated by the key transformation of an enamine-type activation involving the addition of a secondary amine to an alkyne, which enables the subsequent incorporation of aldehydes and ureas/thioureas. This protocol tolerates a broad range of aryl- or alkylaldehydes, N-substituted and unsubstituted ureas/thioureas and alkynes to yield the corresponding DHPMs with specific regioselectivity.

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“…The reaction of N,N-dialkyl-ortho-diaminobenzene 149 [104,105] with aldehydes and ketones in the presence of Lewis acid led to a 1,6-hydride shift and cyclization at the α-carbon atom of the dialkylamino group with the formation of a C-N bond and formation of the benzimidazole 150. 1,2-Diaza-1,3-butadienes 151, containing allyl(propargyl)sulfanyl and cyclic dialkylamino groups, produced 1,2,4-triazines 152 by thermal cyclization [106,107].…”

Section: -92%mentioning

confidence: 99%

tert-Amino effect: the Meth-Cohn and Reinhoudt reactions (Review)

Platonova

Глухарева

Zimovets

et al. 2013

Chem Heterocycl Comp

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The term "tert-amino effect" was proposed in 1972 [1] for the cyclization reactions of tertiary anilines containing various double bonds at the ortho position. Meth-Cohn and Suschitzky [1] referred to the first observation of the tert-amino effect by Pinnow in 1895 [2]. Many different examples of reactions involving the tert-amino effect have now accumulated, and it clearly is a convenient method for the synthesis of an impressive number of nitrogen-containing heterocycles that otherwise might be difficult to obtain. Reviews were published by Reinhoudt in 1990 [3] and by Meth-Cohn in 1996 [4] on heterocyclization reactions that take place by the mechanism of the tert-amino effect. Another review dedicated to 1,6-and 1,8-naphthiridine derivatives was published in 2003 by Quintela [5]. In the review [6] that we published in 2005, attention was focused on the use of such reactions for the synthesis of spiro compounds. In the review [7], published in 2006, the cyclization reactions of ortho-vinylanilines and their heterocyclic aza analogs were considered, and classification according to the method of ring formation was proposed.

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One-Pot Synthesis of 2,3-Dihydro-1H-benzimidazoles

Abstract: A convenient one-pot method for the synthesis of 2,3-dihydro-1H-benzimidazoles has been elaborated. A set of 2,3-dihydro-1H-benzimidazoles was prepared from various ortho-dialkylaminoanilines and aldehydes using Me3SiCl as a condensation agent and pyridine as a basic medium.

Cited by 28 publications

References 14 publications

The Redox‐Neutral Approach to CH Functionalization

The Redox‐Neutral Approach to CH Functionalization

Secondary amine-initiated three-component synthesis of 3,4-dihydropyrimidinones and thiones involving alkynes, aldehydes and thiourea/urea

tert-Amino effect: the Meth-Cohn and Reinhoudt reactions (Review)

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