Ethyl 11a,12-Dihydrobenzo[b]benzo[5,6][1,4]oxazino[2,3-e][1,4]oxazine-5a(6H)-carboxylate
Round 1
Reviewer 1 Report
This short paper describes unexpected and interesting formation of a simple but novel heterocyclic compound which is fully characterised including an X-ray structure. It can be published with just a few corrections and improvements:
Page 1, line 13 - change to "used in the construction" and "not only for"
Page 1, line 14 - change to "but also for novel"
Page 1, line 18 - change to "structure of the newly"
Page 1, line 23 - change o-aminphenole to o-aminophenol.
Page 1, line 26 - change to "is a well-known"Page 1, line 31 - change 'penyl' to 'phenyl'
Page 1, line 39/40 - o-aminophenol is not mentioned and should be added.
Page 1, line 42 - change 'According NMR' to 'According to NMR'
Page 2, Scheme 1 - the structure shown for 1 should show that the H and E groups are cis (wedge bonds). The ring junction could have been trans and the X-ray clearly shows it is cis. The relative configuration in compound 3 should similarly be shown if indeed it is known from the work of ref [6].
Page 2, line 52 and 61 - change o-aminphenole to o-aminophenol.
Page 2/3 - general comment - make the captions to schemes 1 and 2 and Figure 1 be much neater by adding a single space in the middle of the compound name so as to fill the first lines. Also these captions need to be in smaller font and separated off more clearly from the main text, achieved using styles in template.
Page 2, line 62 - change 'other' to 'another'
Page 2, Figure 1 caption - this could be more accurate e.g. - "X-Ray structure (ORTEP at 50% level) of...."
Page 3, line 107 - change compound number to 1.
Page 3, line 108 - change "0- -5" to "0–5" or does it mean zero to minus 5 in which case 0....–5 can be used.
Page 4, line 117 - There is no point in having (ppm, J/Hz) at the start of the NMR then also repeating Hz at each coupling constant. Either keep this part and delete Hz from each entry or leave the entries the same and delete J/Hz at the start.
Page 4, line 118 - the coupling of 4.4 Hz (2 decimal places is unrealistic) must be to NH so the 2H NH signal can't be a 9.2 Hz doublet. I suggest just saying it is a broad singlet which is what it looks from the spectrum. Any apparent doublet may in fact be two singlets due to the NHs being different (and one coupled to CH).
Page 4, Table 1 - at 'unit cell dimensions' the item "=90°" appears three times but opposite a, b and c instead of alpha, beta and gamma which are missing. Since this is obvious for an orthorhombic space group, I suggest just deleting these.
Supplementary material
- The title of each figure should have ethyl as a separate first word, not linked to the rest of the name by a hyphen. Also the compound number should be 1 not 2 (x5). Otherwise satisfactory.
Author Response
Page 1, line 13 - change to "used in the construction" and "not only for"
Page 1, line 14 - change to "but also for novel"
Page 1, line 18 - change to "structure of the newly"
Page 1, line 23 - change o-aminphenole to o-aminophenol.
Page 1, line 26 - change to "is a well-known"Page 1, line 31 - change 'penyl' to 'phenyl'
Page 1, line 39/40 - o-aminophenol is not mentioned and should be added.
Page 1, line 42 - change 'According NMR' to 'According to NMR'
Page 2, line 52 and 61 - change o-aminphenole to o-aminophenol.
Page 2/3 - general comment - make the captions to schemes 1 and 2 and Figure 1 be much neater by adding a single space in the middle of the compound name so as to fill the first lines. Also these captions need to be in smaller font and separated off more clearly from the main text, achieved using styles in template.
Page 2, line 62 - change 'other' to 'another'
Page 2, Figure 1 caption - this could be more accurate e.g. - "X-Ray structure (ORTEP at 50% level) of...."
Page 3, line 107 - change compound number to 1.
Page 3, line 108 - change "0- -5" to "0–5" or does it mean zero to minus 5 in which case 0....–5 can be used.
Page 4, line 117 - There is no point in having (ppm, J/Hz) at the start of the NMR then also repeating Hz at each coupling constant. Either keep this part and delete Hz from each entry or leave the entries the same and delete J/Hz at the start.
Page 4, line 118 - the coupling of 4.4 Hz (2 decimal places is unrealistic) must be to NH so the 2H NH signal can't be a 9.2 Hz doublet. I suggest just saying it is a broad singlet which is what it looks from the spectrum. Any apparent doublet may in fact be two singlets due to the NHs being different (and one coupled to CH).
Page 4, Table 1 - at 'unit cell dimensions' the item "=90°" appears three times but opposite a, b and c instead of alpha, beta and gamma which are missing. Since this is obvious for an orthorhombic space group, I suggest just deleting these.
Authors reply: All necessary corrections were made as requested by Reviewer.
Page 2, Scheme 1 - the structure shown for 1 should show that the H and E groups are cis (wedge bonds). The ring junction could have been trans and the X-ray clearly shows it is cis. The relative configuration in compound 3 should similarly be shown if indeed it is known from the work of ref [6].
Authors reply: The ring junction was shown in Scheme 1 as cis for H and E groups. Unfortunately, there is no information in the ref. 6 about the configuration in compound 3, and we leave the Scheme 3 as it was.
Supplementary material. The title of each figure should have ethyl as a separate first word, not linked to the rest of the name by a hyphen. Also the compound number should be 1 not 2 (x5). Otherwise satisfactory.
Authors reply: All necessary corrections were made as requested by Reviewer.
Reviewer 2 Report
It is a very short communication about obtained molecule and the crystal structure . The material is fully characterized but I have one concern bout the MS spectrum available in the supporting information. On Figure S4 there is a m/z signal with similar isotopic pattern at 311. Is it somehow correlated with expected compound? In general the presented synthetic approach has been previously reported and it is an application of known procedure to new reagents. From scientific point of view this contribution is not adding novel fundamentals to organic synthesis and the overall merit value is rather low. I would suggest an improvement of Figure 1 and showing another view of presented Newman projection along C4-C5 bond what in my opinion will give additional information about these molecule.
Author Response
- I have one concern bout the MS spectrum available in the supporting information. On Figure S4 there is a m/z signal with similar isotopic pattern at 311.
Authors reply: The weak peak of 311 is observed due to extrusion of the proton from N-H bond the molecule in mass-spectrum.
- I would suggest an improvement of Figure 1 and showing another view of presented Newman projection along C4-C5 bond what in my opinion will give additional information about these molecule.
Authors reply: We tried to get the best Newman projection of the molecule and found that the view presented in the paper is the best that we could achieve.
