About reactivity of isomeric azaindoles

Yakhontov, L. N.; Azimov, V. A.; Lapan, E. I.

doi:10.1016/s0040-4039(01)88044-8

Cited by 44 publications

(6 citation statements)

References 5 publications

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“…Halogenation of indole ( 3a ) with ICl in pyridine produced 3-iodoindole, which was immediately converted to its N -Boc derivative ( 4a ) by treatment with Boc 2 O in the presence of DMAP. (For compounds 3d , 3e , and 3f , we proceeded via the previously reported bromination rather than iodination procedure to generate the known 3-bromo derivatives.) Lithium−halogen exchange on derivative 4a induced by the reaction with n -BuLi in the presence of TMEDA at −78 °C generated an anion which was trapped with Bu 3 SnCl to give 5a .…”

Section: Chemistrymentioning

confidence: 99%

Novel Non-Nucleoside Inhibitors of Human Immunodeficiency Virus Type 1 Reverse Transcriptase. 6. 2-Indol-3-yl- and 2-Azaindol-3-yl- dipyridodiazepinones

et al. 1997

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Section: Chemistrymentioning

confidence: 99%

Novel Non-Nucleoside Inhibitors of Human Immunodeficiency Virus Type 1 Reverse Transcriptase. 6. 2-Indol-3-yl- and 2-Azaindol-3-yl- dipyridodiazepinones

et al. 1997

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“…At present, some achiral synthetic methods to prepare azaindolines have been reported, and most of them are mainly used to prepare 5- or 7-azaindolines. − In addition, three works relative to the enantioselective synthesis of azaindolines − have been reported. However, the asymmetric synthesis of 4-azaindolines has been rarely reported, and most of the existing synthetic methods are relatively complicated including intramolecular carbolithiation, ortho-directed lithiation of carbamate, acid-catalyzed annulation of aminopyridines, and C−H activation. , To the best of our knowledge, only one of them has been successfully used to synthesize 4-azaindolines with high enantioselectivity .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 4-Azaindolines Using Phase-Transfer Catalysis via an Intramolecular Mannich Reaction

et al. 2020

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A series of bifunctional asymmetric phase-transfer catalysts containing novel fluorine-containing urea groups derived from cinchona alkaloids have been synthesized and successfully applied in the asymmetric intramolecular Mannich reaction. The 4-azaindoline products bearing multiple substrates were obtained in excellent yield (90−99%), with high enantioselectivity (up to 95%) and diastereoselectivity (up to >99:1).

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“…4-Azaindole was first prepared by Kruber in 1943. [11] To date, one of the most commonly used method for the preparation of 4-azainole was the same as those for indoles including the Madelung-type cyclization, [12] a Reissert-type procedure, [13][14][15][16] the Leimgruber-Batcho reaction, [17,18] and a Lorenz-type cyclization. [18,19] Recently, several groups have utilized a reductive cyclization methodology for the construction of azaindoles starting from acetylenes and iodinated amino-pyridines.…”

Section: Introductionmentioning

confidence: 99%