A simple synthesis of aminopyridines: use of amides as amine source

Kodimuthali, Arumugam; Mungara, Anitha; Prasunamba, Padala Lakshmi; Pal, Manojit

doi:10.1590/s0103-50532010000800005

Cited by 21 publications

(22 citation statements)

References 12 publications

(13 reference statements)

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“…Further evaluation showed that potassium tert-butoxide was the best base for this transformation because it afforded the desired product 2a in 85% yield (entry 7). Other solvents (DMSO, DCE, THF, 1,4-dioxane, toluene, and cyclohexane) were subsequently screened, and N,N-dimethylformamide proved to be the most efficient solvent (entries [8][9][10][11][12][13]. A control experiment showed that no reaction occurred without the addition of 4-toluenesulfonyl chloride (entry 14).…”

Section: Paper Syn Thesismentioning

confidence: 99%

“…The crude product was purified by chromatography (silica gel, PE-EtOAc, 15:1-10:1) to provide the corresponding product 2. 13 C NMR (100 MHz, CDCl 3 ): δ = 21. 6, 41.8, 115.0, 124.0, 125.5, 125.6, 128.2, 128.7, 128.9, 130.8, 137.8, 137.9, 153.0, 159.5, 163.9.…”

Section: -(Dimethylamino)quinazolines 2; General Proceduresmentioning

confidence: 99%

“…3 41.9, 114.4, 124.2, 125.4, 125.7, 128.6, 130.4, 131.0, 131.9, 137.2, 139.6, 152.7, 162.5, 163.6. 8, 115.0, 124.0, 125.5, 128.2, 128.4, 128.7, 130.0, 132.0, 139.0, 153.0, 159.3, 163. 8, 55.3, 113.6, 114.8, 123.7, 125.5, 128.5, 130.0, 131.6, 131.9, 153.1, 159.1, 161.4, 163.9 7, 56.0, 110.8, 111.6, 114.8, 121.7, 123.7, 125.5, 128.5, 131.9, 148.9, 151.1, 153.0, 159.0, 163.9 3, 41.7, 111.7, 114.7, 123.1, 125.5, 126.9, 128.3, 129.7, 131.7, 152.0, 153.2, 159.7, 163.9 13 C NMR (100 MHz, CDCl 3 ): δ = 41. 8, 114.9, 124.3, 125.5, 128.4, 128.6, 129.8, 130.9, 132.2, 137.3, 152.7, 158.2, 163.9.…”

Section: -(Dimethylamino)quinazolines 2; General Proceduresmentioning

confidence: 99%

“…IR (KBr): 2929, 1621, 1354, 1316 H NMR (400 MHz, CDCl 3 ): δ = 3.40 (s, 6 H), 7.36 (t,J = 7.2 Hz,1 H),3 H),7.92 (d,J = 8.0 Hz,1 H),7.99 (d,J = 8.4 Hz, 1 H), 8.65 (d, J = 8.0 Hz, 2 H). 13 C NMR (100 MHz, CDCl 3 ): δ = 41. 7,115.1,124.4,125.1,125.5,128.7,131.6,132.1,142.4,152.8,157.8,163.8 7.41 (t,J = 7.6 Hz,1 H),3 H),7.93 (d,J = 8.4 Hz,1 H),8.04 (d,J = 8.4 Hz, 1 H), 8.65 (d, J = 8.8 Hz, 2 H).…”

Section: -(Dimethylamino)-2-[4-(trifluoromethyl)phenyl]quinazoline (2l)mentioning

confidence: 99%

“…7,115.1,124.4,125.1,125.5,128.7,131.6,132.1,142.4,152.8,157.8,163.8 7.41 (t,J = 7.6 Hz,1 H),3 H),7.93 (d,J = 8.4 Hz,1 H),8.04 (d,J = 8.4 Hz, 1 H), 8.65 (d, J = 8.8 Hz, 2 H). 13 C NMR (100 MHz, CDCl 3 ): δ = 41. 8, 113.1, 115.1, 119.1, 124.8, 125.5, 128.8, 132.0, 132.3, 143.2, 152.8, 157.3, 163.8 2 H),7.67 (t,J = 7.8 Hz,1 H),1 H),7.92 (d,J = 8.8 Hz,1 H),3 H),8.69 (d,J = 8.4 Hz, 1 H), 9.07 (s, 1 H).…”

Section: -(Dimethylamino)-2-[4-(trifluoromethyl)phenyl]quinazoline (2l)mentioning

confidence: 99%

See 4 more Smart Citations

Synthesis of 4-(Dimethylamino)quinazoline via Direct Amination of Quinazolin-4(3H)-one Using N,N-Dimethylformamide as a Nitrogen Source at Room Temperature

et al. 2015

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1) TsCl, Na 2 CO 3 THF 2) DMF, KOt-Bu r.t., 1 h 60-89% R 1 = aryl, heteroaryl R 2 = Me, Br Abstract An efficient direct amination of quinazolin-4(3H)-ones using N,N-dimethylformamide as a nitrogen source is described that affords the corresponding 4-(dimethylamino)quinazolines in high yields. This transformation proceeds through efficient 4-toluenesulfonyl chloride mediated C-OH bond activation at room temperature.

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Section: Paper Syn Thesismentioning

confidence: 99%

Section: -(Dimethylamino)quinazolines 2; General Proceduresmentioning

confidence: 99%

Section: -(Dimethylamino)quinazolines 2; General Proceduresmentioning

confidence: 99%

Section: -(Dimethylamino)-2-[4-(trifluoromethyl)phenyl]quinazoline (2l)mentioning

confidence: 99%

Section: -(Dimethylamino)-2-[4-(trifluoromethyl)phenyl]quinazoline (2l)mentioning

confidence: 99%

See 3 more Smart Citations

Synthesis of 4-(Dimethylamino)quinazoline via Direct Amination of Quinazolin-4(3H)-one Using N,N-Dimethylformamide as a Nitrogen Source at Room Temperature

et al. 2015

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Room‐Temperature Dialkylamination of Chloroheteroarenes Using a Cu(II)/PTABS Catalytic System

Shet

Patel

Waikar

et al. 2022

Chemistry An Asian Journal

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The dimethylamino functionality has significant importance in industrially relevant molecules and methodologies to install these efficiently are highly desirable. We report herein a highly efficient, room‐temperature dimethylamination of chloroheteroarenes performed via the in‐situ generation of dimethylamine using N,N‐dimethylformamide (DMF) as precursor wiith a large substrate scope that includes various heteroarenes, purines as well as commercially relevant drugs such as altretamine, ampyzine and puromycin precursor.

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Photoassisted Charge Transfer Between DMF and Substrate: Facile and Selective N,N‐Dimethylamination of Fluoroarenes

et al. 2021

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A reversible Van der Waals complex formation between the electron‐deficient fluorinated aromatic ring and N,N‐dimethylformamide (DMF) molecules followed by light irradiation resulted in charge transfer (CT) process. The complex was stabilized by ammonium formate and further decomposed to form the C−N bond. Control experiments revealed that the simultaneous SNAr pathway also contributes to product formation. This methodology is mild, metal‐free, and effective for the amination of a variety of substrates. The reproducibility of this methodology was also verified on gram‐scale reactions. The CT states were supported by control UV/Vis spectroscopy and computational studies.

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A simple synthesis of aminopyridines: use of amides as amine source

Cited by 21 publications

References 12 publications

Synthesis of 4-(Dimethylamino)quinazoline via Direct Amination of Quinazolin-4(3H)-one Using N,N-Dimethylformamide as a Nitrogen Source at Room Temperature

Synthesis of 4-(Dimethylamino)quinazoline via Direct Amination of Quinazolin-4(3H)-one Using N,N-Dimethylformamide as a Nitrogen Source at Room Temperature

Room‐Temperature Dialkylamination of Chloroheteroarenes Using a Cu(II)/PTABS Catalytic System

Photoassisted Charge Transfer Between DMF and Substrate: Facile and Selective N,N‐Dimethylamination of Fluoroarenes

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