Allylation and cyanation of aza-aromatics activated by chloroformate and a catalytic amount of iodine

Yadav, J. S.; Reddy, B. V. Subba; Srinivas, M.; Sathaiah, K.

doi:10.1016/j.tetlet.2005.03.127

Tetrahedron Letters

2005

DOI: 10.1016/j.tetlet.2005.03.127

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Allylation and cyanation of aza-aromatics activated by chloroformate and a catalytic amount of iodine

J. S. Yadav

B. V. Subba Reddy

M. Srinivas

et al.

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Cited by 30 publications

(3 citation statements)

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“…The bond lengths of 2.846(3) (Ca1-C6) and 2.813(3) (Ca1-C13) lie in the range of calcium-carbon bonds observed for the triglyme adduct of bisA C H T U N G T R E N N U N G (h 3 -allyl)calcium and exclude s-bound carbanionic ligands. [24] The Ca1-N1 and Ca1-N2 bond lengths of 2.407(2) and 2.4331 (19) are somewhat longer than those in 9 a·A C H T U N G T R E N N U N G (THF) 4 …”

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confidence: 98%

Calcium‐Mediated Dearomatization, CH Bond Activation, and Allylation of Alkylated and Benzannulated Pyridine Derivatives

Jochmann

Leich

Spaniol

et al. 2011

Chemistry A European J

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A facile and general synthetic pathway for the production of dearomatized, allylated, and C-H bond activated pyridine derivatives is presented. Reaction of the corresponding derivative with the previously reported reagent bis(allyl)calcium, [Ca(C(3)H(5))(2)] (1), cleanly affords the product in high yield. The range of N-heterocyclic compounds studied comprised 2-picoline (2), 4-picoline (3), 2,6-lutidine (4), 4-tert-butylpyridine (5), 2,2'-bipyridine (6), acridine (7), quinoline (8), and isoquinoline (9). Depending on the substitution pattern of the pyridine derivative, either carbometalation or C-H bond activation products are obtained. In the absence of methyl groups ortho or para to the nitrogen atom, carbometalation leads to dearomatized products. C(sp(3))-H bond activation occurs at ortho and para situated methyl groups. Steric shielding of the 4-position in pyridine yields the ring-metalated product through C(sp(2))-H bond activation instead. The isolated compounds [Ca(2-CH(2)-C(5)H(4)N)(2)(THF)] (2b⋅(THF)), [Ca(4-CH(2)-C(5)H(4)N)(2)(THF)(2)] (3b⋅(THF)(2)), [Ca(2-CH(2)-C(5)H(3)N-6-CH(3))(2)(THF)(n)] (4b⋅(THF)(n); n=0, 0.75), [Ca{2-C(5)H(3)N-4-C(CH(3))(3)}(2)(THF)(2)] (5c⋅(THF)(2)), [Ca{4,4'-(C(3)H(5))(2)-(C(10)H(8)N(2))}(THF)] (6a⋅(THF)), [Ca(NC(13) H(9)-9-C(3)H(5))(2)(THF)] (7a⋅(THF)), [Ca(4-C(3) H(5)-C(9) H(7)N)(2)(THF)] (8b⋅(THF)), and [Ca(1-C(3)H(5)-C(9)H(7) N)(2)(THF)(3)] (9a⋅(THF)(3)) have been characterized by NMR spectroscopy and metal analysis. 9a⋅(THF)(4) and 4b⋅(THF)(3) were additionally characterized in the solid state by X-ray diffraction experiments. 4b⋅(THF)(3) shows an aza-allyl coordination mode in the solid state. Based on the results, mechanistic aspects are discussed in the context of previous findings.

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confidence: 98%

Calcium‐Mediated Dearomatization, CH Bond Activation, and Allylation of Alkylated and Benzannulated Pyridine Derivatives

Jochmann

Leich

Spaniol

et al. 2011

Chemistry A European J

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“…8 Besides different synthetic strategies, 8 in 1997 Yamaguchi et al reported an unexpected synthesis of 1,3-disubstituted benzoisoquinuclidines upon double nucleophilic addition and cyclization of N -acylated isoquinolinium triflate salts with allyl trimethylsilane (Scheme 1b). 9…”

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confidence: 99%

Divergent access to fused N-heterocycle-thiazolines by solvent-dependent reaction of isoquinolinium thiolates with silylketene acetals

et al. 2023

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“…We next evaluated a number of transformations of the enecarbamate moiety of the 1,2-dihydroisoquinoline scaffolds 2b) . After evaluation of Lewis acid promoters, we found that the bridged, exocyclic enecarbamate 24 was formed in 84% yield when scaffold 23 was treated with TMSOTf/ N,N -diisopropylethylamine (DIEA) (CH 2 Cl 2 , −78 → −20 °C) …”

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confidence: 99%

1,2-Dihydroisoquinolines as Templates for Cascade Reactions To Access Isoquinoline Alkaloid Frameworks

Porco

2007

Org. Lett.

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Allylation and cyanation of aza-aromatics activated by chloroformate and a catalytic amount of iodine

Cited by 30 publications

References 14 publications

Calcium‐Mediated Dearomatization, CH Bond Activation, and Allylation of Alkylated and Benzannulated Pyridine Derivatives

Calcium‐Mediated Dearomatization, CH Bond Activation, and Allylation of Alkylated and Benzannulated Pyridine Derivatives

Divergent access to fused N-heterocycle-thiazolines by solvent-dependent reaction of isoquinolinium thiolates with silylketene acetals

1,2-Dihydroisoquinolines as Templates for Cascade Reactions To Access Isoquinoline Alkaloid Frameworks

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