Nucleophilic Substitution of Benzotriazolylalkyl Chlorides with Grignard Reagents: A Direct Route to Benzotriazoloalkyl(hetero)aromatic Compounds

Katritzky, Alan R.

doi:10.1055/s-1999-3662

Cited by 6 publications

(1 citation statement)

References 16 publications

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“…R f = 0.43 (eluent: hexane/ethyl acetate (9:1)); yield: 36.6 mg (58%); off-white solid; mp 134–136 °C (lit . mp 128–130 °C); 1 H NMR (300 MHz, CDCl 3 ): δ 8.08 (d, J = 8.1 Hz, 1H), 7.45–7.32 (m, 3H), 6.84–6.74 (m, 3H), 5.93 (s, 2H), 5.74 (s, 2H); 13 C{ 1 H} NMR (75 MHz, CDCl 3 ): δ 148.3, 147.8, 146.3, 132.7, 128.4, 127.4, 124.0, 121.3, 120.1, 109.7, 108.5, 108.1, 101.3, 52.2; IR (KBr, cm –1 ): 3061, 2978, 2914, 1614, 1489, 1449, 1250, 1088, 758, 740; GC/MS ( m / z , %): 253 (100.0), 224 (47.0), 167 (45.8), 135 (85.4), 77 (60.8).…”

Section: Experimental Sectionmentioning

confidence: 99%

Exploring Possible Surrogates for Kobayashi’s Aryne Precursors

Muraca

Raminelli

2020

ACS Omega

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A class of aryne precursors, that is, 2-(trimethylsilyl)aryl 4-chlorobenzenesulfonates, has been developed through well-established synthetic routes, which allow the formation of arynes under relatively mild conditions. All the aryne precursors were obtained from phenols and 4-chlorobenzenesulfonyl chloride, an inexpensive and easy-to-handle reagent with relatively low toxicity, and subjected to nucleophilic addition reactions, providing addition products in yields of 24 to 92%, and to cycloaddition reactions, affording cycloadducts in yields up to 80%. This work provides interesting insights into the mechanisms of aryne generation. In addition, 2-(trimethylsilyl)phenyl 4-chlorobenzenesulfonate was successfully employed in the total synthesis of (±)-aporphine.

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Section: Experimental Sectionmentioning

confidence: 99%

Exploring Possible Surrogates for Kobayashi’s Aryne Precursors

Muraca

Raminelli

2020

ACS Omega

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One‐Pot Synthesis of N‐Alkyl Benzotriazoles via a Brønsted Acid‐Catalyzed Three‐Component Reaction

et al. 2017

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A novel three‐component condensation reaction of benzotriazoles, aldehydes and tertiary anilines efficiently catalyzed by readily available organic acid p‐toluenesulfonic acid (PTSA) has been developed. A series of N‐alkyl benzotriazoles were synthesized in up to 97% yield for 21 examples starting from anilines, benzotriazoles and formaldehyde. This strategy features a simple system, atom economy, environmental friendliness, high efficiency, excellent regioselectivity, good functional group tolerance, easily available starting materials, and cheap catalyst. The mechanistic studies indicated that aza quinone methide was probably involved as an intermediate in this transformation.magnified image

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ChemInform Abstract: Nucleophilic Substitution of Benzotriazolylalkyl Chlorides with Grignard Reagents: A Direct Route to Benzotriazoloalkyl(hetero)aromatic Compounds.

et al. 1999

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Nucleophilic Substitution of Benzotriazolylalkyl Chlorides with Grignard Reagents: A Direct Route to Benzotriazoloalkyl(hetero)aromatic Compounds

Abstract: Benzotriazolylalkyl chlorides 5 react with (hetero)aromatic Grignard reagents generated from the corresponding halogen derivatives to afford benzotriazoloalkyl(hetero)aromatic compounds 8a-k and 10a-c in good yields.

Cited by 6 publications

References 16 publications

Exploring Possible Surrogates for Kobayashi’s Aryne Precursors

Exploring Possible Surrogates for Kobayashi’s Aryne Precursors

One‐Pot Synthesis of N‐Alkyl Benzotriazoles via a Brønsted Acid‐Catalyzed Three‐Component Reaction

ChemInform Abstract: Nucleophilic Substitution of Benzotriazolylalkyl Chlorides with Grignard Reagents: A Direct Route to Benzotriazoloalkyl(hetero)aromatic Compounds.

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