(Z)-6-((Dimethylamino)methylene)-2-methyl-2,3-dihydroimidazo[2,1-b]thiazol-5(6H)-one

Round 1

Reviewer 1 Report

Comments and Suggestions for Authors

Comments

The manuscript entitled " (Z)-6-((dimethylamino)methylene)-2-methyl-2,3-dihydroimidazo[2,1-b]thiazol-5(6H)-one" describes the synthesis of a novel imidazothiazole. The work is scientifically sound and addresses a relevant topic. However, the manuscript requires revision before acceptance. The following points should be addressed:

1. The authors need to provide 1-2 concrete examples demonstrating how compound 2 can be utilized in subsequent synthetic transformations to construct more complex heterocyclic systems. This can strengthen the rationale for synthesizing compound 2.
2. The authors need to provide details on reaction optimization. Was any optimization performed regarding different molar ratios of DMF-DMA or reaction conditions to achieve better yield?
3. How did the authors confirm Z-configuration in the product? The authors need to add 2D NMR data or provide X-ray crystal structure data to support the Z-configuration. Since compound 2 was recrystallized and obtained as crystals, single-crystal X-ray diffraction analysis would provide unambiguous confirmation of the stereochemistry.
4. The authors need to include a structure showing carbon numbering consistent with the ¹³C NMR assignments mentioned in the text to help readers correlate the NMR signals with specific positions in the molecule.
5. In lines 94 and 116, incorrect ¹³C frequency (should be ~125 MHz, not 100 MHz).
6. In line 95, typographical error should be fixed (“Paulo Alto” → “Palo Alto”)
7. In line 113, fix the duplicated "3.13 (s, 3Н, NСН₃), 3.42".
8. In references 8, 9, 14, 21, 23–25, page numbers are missed.
9. In reference 4, the publication year should be 2020.
10. In reference 13, the publication year should be 2023.

Author Response

Dear Editor and Reviewer,

We would like to thank you for the review of our article and extremely valuable and constructive comments that helped to improve this manuscript. We agree with your suggestions, and relevant corrections have been incorporated in the revised version of the manuscript (please see the text of the revised manuscript marked with color).

Reviewer 1

Many thanks for your valuable suggestions and remarks concerning our manuscript. Additionally, we would like to address some of the issues you have raised:

Reviewer #1: “The manuscript entitled " (Z)-6-((dimethylamino)methylene)-2-methyl-2,3-dihydroimidazo[2,1-b]thiazol-5(6H)-one" describes the synthesis of a novel imidazothiazole. The work is scientifically sound and addresses a relevant topic. However, the manuscript requires revision before acceptance. The following points should be addressed”:

1. The authors need to provide 1-2 concrete examples demonstrating how compound 2 can be utilized in subsequent synthetic transformations to construct more complex heterocyclic systems. This can strengthen the rationale for synthesizing compound 2.

We thank the reviewer for this valuable suggestion. To clarify the synthetic relevance of compound 2, additional sentences were added to the Introduction section, highlighting its potential use as an intermediate for the preparation of more complex heterocyclic derivatives.

2. The authors need to provide details on reaction optimization. Was any optimization performed regarding different molar ratios of DMF-DMA or reaction conditions to achieve better yield?

We appreciate the reviewer’s comment. The optimization of reaction conditions was indeed performed, and the relevant details, including the influence of the DMF-DMA molar ratio and temperature on the reaction yield, have now been added to the "Results and Discussion" section.

3. How did the authors confirm Z-configuration in the product? The authors need to add 2D NMR data or provide X-ray crystal structure data to support the Z-configuration. Since compound 2 was recrystallized and obtained as crystals, single-crystal X-ray diffraction analysis would provide unambiguous confirmation of the stereochemistry.

We thank the reviewer for this valuable comment. To unambiguously confirm the Z-configuration of compound 2, additional 1D and 2D NMR experiments were conducted. The results clearly support the assigned configuration and have been incorporated into the revised manuscript and supplementary file.

4. The authors need to include a structure showing carbon numbering consistent with the ¹³C NMR assignments mentioned in the text to help readers correlate the NMR signals with specific positions in the molecule.

We thank the reviewer for this suggestion. A structure with carbon numbering consistent with the 13C NMR assignments has been included in the revised manuscript.

5. In lines 94 and 116, incorrect ¹³C frequency (should be ~125 MHz, not 100 MHz).

Thank you for your remark and suggestion, we corrected it as suggested

6. In line 95, typographical error should be fixed (“Paulo Alto” → “Palo Alto”)

Thank you for your remark and suggestion, we corrected it as suggested

7. In line 113, fix the duplicated "3.13 (s, 3Н, NСН₃), 3.42".

Thank you for your remark and suggestion, we corrected it as suggested

8. In references 8, 9, 14, 21, 23–25, page numbers are missed.

Thank you for your remark and suggestion, we corrected it as suggested

9. In reference 4, the publication year should be 2020.

Thank you for your remark and suggestion, we corrected it as suggested

10. In reference 13, the publication year should be 2023.

Thank you for your remark and suggestion, we corrected it as suggested

Round 2

Reviewer 1 Report

Comments and Suggestions for Authors

All the earlier comments have been addressed well. The revised manuscript is clear, accurate, and nicely organized. The added structural details and corrected NMR information make the paper easier to follow. The references and minor errors have also been fixed properly. Overall, the work looks good now and can be accepted in the present form.