4-Amino-5-benzoyl-1-benzyl-2-(4,5,6,7-tetrahydro-1H-indol-2-yl)-1H-pyrrole-3-carbonitrile
Round 1
Reviewer 1 Report
This manuscript describes the first synthesis of 4-Amino-5-benzoyl-1-benzyl-2-(4,5,6,7-tetrahydro-1H-indol-2-yl)-1H-pyrrole-3-carbonitrile, a derivative of 2,2’-pyrrole. The method is adequately described, and the compound is full characterized by 1H-NMR, 13C-NMR, IR spectroscopy, and elemental analysis.
Overall, the manuscript was well organized and written and can be published on Molbank after minor revisions.
Line 35-36. Compound 1-benzyl-3-imino-5,6,7,8-tetrahydro-3H-pyrrolo- 35 [1,2-a]indol-1-amine (2) couldn’t be founded in the cited reference [14]. Please delete this reference or add the correct one.
Line 50. The title of Scheme 2 needs to be corrected. Regarding the mechanism, it could be useful to add a comment on the new chiral center created after the carbanion attack on the nitrile’s electrophilic carbon.
Line 51-52. IR spectra were missing in the supplementary materials archive.
Line 73. Should be refluxed.
Author Response
Dear Ms. Gao,
Please find attached the revised manuscript entitled “4-Amino-5-benzoyl-1-benzyl-2-(4,5,6,7-tetrahydro-1H-indol-2-yl)-1H-pyrrole-3-carbonitrile” by Olga V. Petrova et al. amended according to the reviewers comments and suggestions.
First of all, please thank reviewer on our behalf for the fair and genuine work with our manuscript and the very useful and constructive suggestions and advises which we accepted and followed to.
The following alterations have been made in the manuscript:
Reviewer wrote:
1: Compound 1-benzyl-3-imino-5,6,7,8-tetrahydro-3H-pyrrolo- 35 [1,2-a]indol-1-amine (2) couldn’t be founded in the cited reference [14]. Please delete this reference or add the correct one.
Answer:
The reference 14 was deleted from phrase “the reaction of easily available [14] 1-benzyl-3-imino-5,6,7,8-tetrahydro-3H-pyrrolo-[1,2-a]indol-1-amine (2) and 1-chloroacetophenone in K2CO3/MeCN system”
2: The title of Scheme 2 needs to be corrected. Regarding the mechanism, it could be useful to add a comment on the new chiral center created after the carbanion attack on the nitrile’s electrophilic carbon.
Answer:
The title of Scheme 2 needs was corrected.
On the advice of the respected reviewer, we have changed the following paragraph by adding the comments on the formation of the new chiral center to it.
“The latter undergo the proton abstraction from the active CH2 group, then carbanion B thus obtained intramolecularly attacks the nitrile’s electrophilic carbon with simultaneous the pyrrolizine ring-opening and formation of iminopyrroline C with chiral center. Its further aromatization via the proton transfer from asymmetric carbon atom to imino-group finishes this process.”
3: IR spectra were missing in the supplementary materials.
Answer:
IR spectrum was inserted in the supplementary materials.
4: Line 73. Should be refluxed.
“reflux” was replaced with “refluxed”
Best regards,
Lyubov Sobenina
