The tellurium–lithium exchange reaction: selective functionalization of electron-deficient heteroaromatics

Sugimoto, Osamu; Sudo, Muneyoshi; Tanji, Ken‐ichi

doi:10.1016/s0040-4020(01)00089-8

Cited by 19 publications

(10 citation statements)

References 14 publications

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“…The absolute structure of 1,1′‐2,6‐naphthyridine ( 13 ) resulting from the reaction of 2,6‐naphthyridine ( 3 ) with LiTMP was determined based on the observation of one singlet signal in the 1 H‐NMR spectrum. The structures of 1,1′‐2,7‐naphthyridine ( 14 ) [ 3a ] , 4,4′‐biquinazoline ( 15 ) [ 10 ] , and 4,4′‐bicinnoline ( 16 ) [ 7b ] were confirmed by comparing the available spectra with the literature data.…”

Section: Synthesis Of Dimeric Diazanaphthalenes Composed Of the Same mentioning

confidence: 98%

One‐pot homo‐ and cross‐coupling of diazanaphthalenes via C‐H substitution: Synthesis of Bis‐ and Tris‐diazanaphthalenes

Uçar

Daştan

2020

Journal of Heterocyclic Chem

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The transition metal‐free coupling reactions of unactivated diazanaphthalenes were studied using only lithium tetramethylpiperidine (LiTMP) reagent. Symmetrical and nonsymmetrical bis‐diazanaphthalenes were synthesized in moderate to high yield by homo‐ and cross‐coupling of related monomers. In addition, the single‐step synthesis of diquinoxalino [2,3‐a: 2', 3'c] phenazine and 2,2': 3', 2″ ‐ terquinoxaline using the appropriate equivalent amount of LiTMP was performed. The products were characterized by means of NMR spectroscopy and HRMS spectrometry.

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Section: Synthesis Of Dimeric Diazanaphthalenes Composed Of the Same mentioning

confidence: 98%

One‐pot homo‐ and cross‐coupling of diazanaphthalenes via C‐H substitution: Synthesis of Bis‐ and Tris‐diazanaphthalenes

Uçar

Daştan

2020

Journal of Heterocyclic Chem

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“…On the other hand, the tellurium-lithium exchange reaction on 1-isoquinolyl telluride 280 has proven useful in the preparation of 1-isoquinolyllithium (275) (Scheme 17.147) [390].…”

Section: Reactions With Oxidizing Reagentsmentioning

confidence: 99%

Six‐Membered Heterocycles: Quinoline and Isoquinoline

Alajarı́n

Burgos

2011

Modern Heterocyclic Chemistry

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“…For example, 7-iodo-3-phenyl-3 H -1,2,3-triazolo[4,5- d ]pyrimidine is lithiated at the 7-position, but this reaction requires −100 °C and gives the corresponding products in low yield. Moreover, lithiation of quinoxaline or quinazoline using tellurium-lithium exchange reaction gave the dimer (2,2‘-biquinoxalinyl or 4,4‘-biquinazolinyl) even at −78 °C …”

mentioning

confidence: 99%

Preparation of Nitrogen-Containing π-Deficient Heteroaromatic Grignard Reagents: Oxidative Magnesiation of Nitrogen-Containing π-Deficient Halogenoheteroaromatics Using Active Magnesium

2003

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The oxidative magnesiation of nitrogen-containing pi-deficient halogenoheteroaromatics using active magnesium was accomplished. Both magnesiation followed by addition of a carbonyl compound (Grignard reaction) and magnesiation in the presence of a carbonyl compound (Barbier reaction) were carried out to afford the corresponding product. Especially, the latter method enabled fused halogenodiazines such as 4-chloro-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine or 2-chloroquinoxaline to magnesiate at a mild temperature (-20 to 30 degrees C).

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The tellurium–lithium exchange reaction: selective functionalization of electron-deficient heteroaromatics

Cited by 19 publications

References 14 publications

One‐pot homo‐ and cross‐coupling of diazanaphthalenes via C‐H substitution: Synthesis of Bis‐ and Tris‐diazanaphthalenes

One‐pot homo‐ and cross‐coupling of diazanaphthalenes via C‐H substitution: Synthesis of Bis‐ and Tris‐diazanaphthalenes

Six‐Membered Heterocycles: Quinoline and Isoquinoline

Preparation of Nitrogen-Containing π-Deficient Heteroaromatic Grignard Reagents: Oxidative Magnesiation of Nitrogen-Containing π-Deficient Halogenoheteroaromatics Using Active Magnesium

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