Synthesis ofN¹‐nitroso‐3‐nitromethylindole: A nonvolatileN‐nitroso compound isolated from the nitrosation of the alkaloid gramine

Verification of preparations of (1H-indol-3-yl)methyl electrophiles and development of their microflow rapid generation and substitution

“…We speculated that the desired 6a formed in situ (it probably had lachrymatory nature), but the undesired polymerization of indole analogues underwent concomitantly that led to its precipitation. The second report by Scanlan et al includes the synthesis of 6a by bromination with TMSCl and LiBr 18 . They reported only TLC analysis for structural confirmation of 6a (Fig.…”

“…Despite these reports, SciFinder search revealed five papers that reported the synthesis of (1 H -indol-3-yl)methyl electrophile 6 (Table 1 ) 15 , 18 – 21 . Two among these also report spectral data for 6 19 , 21 .…”

“…However, based on the previous reports for similar compounds, some discrepancies were identified between the reported and expected data. Three of the five studies involved elemental analysis 15 , TLC analysis 18 , or no analytical data 20 . Besides the aforementioned five studies, five other studies reported nucleophilic substitution of 6 , although the preparation procedure for 6 was not described 22 – 26 .…”

Verification of preparations of (1H-indol-3-yl)methyl electrophiles and development of their microflow rapid generation and substitution

“…We speculated that the desired 6a formed in situ (it probably had lachrymatory nature), but the undesired polymerization of indole analogues underwent concomitantly that led to its precipitation. The second report by Scanlan et al includes the synthesis of 6a by bromination with TMSCl and LiBr 18 . They reported only TLC analysis for structural confirmation of 6a (Fig.…”

“…Despite these reports, SciFinder search revealed five papers that reported the synthesis of (1 H -indol-3-yl)methyl electrophile 6 (Table 1 ) 15 , 18 – 21 . Two among these also report spectral data for 6 19 , 21 .…”

“…However, based on the previous reports for similar compounds, some discrepancies were identified between the reported and expected data. Three of the five studies involved elemental analysis 15 , TLC analysis 18 , or no analytical data 20 . Besides the aforementioned five studies, five other studies reported nucleophilic substitution of 6 , although the preparation procedure for 6 was not described 22 – 26 .…”

Molecular Targets and Anticancer Potential of Indole-3-Carbinol and Its Derivatives

“…In a low pH environment, I3C is converted into polymeric products, and 3,3'-diindolylmethane (DIM) is the main one. 3 DIM is a major in vivo acidcatalyzed condensation product of I3C. In some cruciferous vegetables, indole, N-methoxyindole-3-carbinol (NI3C), is found.…”

Verification of preparations of (1H-indol-3-yl)methyl electrophiles and development of their microflow rapid generation and substitution

“…We speculated that the desired 6a formed in situ (it probably had lachrymatory nature), but the undesired polymerization of indole analogues underwent concomitantly that led to its precipitation. The second report by Scanlan et al includes the synthesis of 6a by bromination with TMSCl and LiBr 18 . They reported only TLC analysis for structural confirmation of 6a (Fig.…”

“…Despite these reports, SciFinder search revealed five papers that reported the synthesis of (1 H -indol-3-yl)methyl electrophile 6 (Table 1 ) 15 , 18 – 21 . Two among these also report spectral data for 6 19 , 21 .…”

“…However, based on the previous reports for similar compounds, some discrepancies were identified between the reported and expected data. Three of the five studies involved elemental analysis 15 , TLC analysis 18 , or no analytical data 20 . Besides the aforementioned five studies, five other studies reported nucleophilic substitution of 6 , although the preparation procedure for 6 was not described 22 – 26 .…”

Molecular Targets and Anticancer Potential of Indole-3-Carbinol and Its Derivatives

“…In a low pH environment, I3C is converted into polymeric products, and 3,3'-diindolylmethane (DIM) is the main one. 3 DIM is a major in vivo acidcatalyzed condensation product of I3C. In some cruciferous vegetables, indole, N-methoxyindole-3-carbinol (NI3C), is found.…”

Verification of preparations of (1H-indol-3-yl)methyl electrophiles and development of their microflow rapid generation and substitution

“…We speculated that the desired 6a formed in situ (it probably had lachrymatory nature), but the undesired polymerization of indole analogues underwent concomitantly that led to its precipitation. The second report by Scanlan et al includes the synthesis of 6a by bromination with TMSCl and LiBr 18 . They reported only TLC analysis for structural confirmation of 6a (Fig.…”

“…Despite these reports, SciFinder search revealed five papers that reported the synthesis of (1 H -indol-3-yl)methyl electrophile 6 (Table 1 ) 15 , 18 – 21 . Two among these also report spectral data for 6 19 , 21 .…”

“…However, based on the previous reports for similar compounds, some discrepancies were identified between the reported and expected data. Three of the five studies involved elemental analysis 15 , TLC analysis 18 , or no analytical data 20 . Besides the aforementioned five studies, five other studies reported nucleophilic substitution of 6 , although the preparation procedure for 6 was not described 22 – 26 .…”

Molecular Targets and Anticancer Potential of Indole-3-Carbinol and Its Derivatives

“…In a low pH environment, I3C is converted into polymeric products, and 3,3'-diindolylmethane (DIM) is the main one. 3 DIM is a major in vivo acidcatalyzed condensation product of I3C. In some cruciferous vegetables, indole, N-methoxyindole-3-carbinol (NI3C), is found.…”