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Volumn 130, Issue 40, 2008, Pages 13222-13224

On the two-component microwave-mediated reaction of isonitriles with carboxylic acids: Regarding alleged formimidate carboxylate mixed anhydrides

Author keywords

[No Author keywords available]

Indexed keywords

ACID ANHYDRIDE; CARBOXYLIC ACID; CARBOXYLIC ACID DERIVATIVE; FORMIMIDATE CARBOXYLATE; ISONITRILE DERIVATIVE; METHANOL; UNCLASSIFIED DRUG;

EID: 53549108902     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja8047078     Document Type: Article
Times cited : (58)

References (52)
  • 5
    • 26844537872 scopus 로고    scopus 로고
    • For reviews, see: c
    • For reviews, see: (c) Banfi, L.; Riva, R. Org. React. 2005, 65, 1.
    • (2005) Org. React , vol.65 , pp. 1
    • Banfi, L.1    Riva, R.2
  • 8
    • 0041417143 scopus 로고    scopus 로고
    • The reaction described here is a special instance of a Mumm rearrangement which involves a 1,3-O→N acyl transfer not in the formimidate series. However, the formimidate context reported here renders this reaction unique. For literature access to the Mumm reaction, see: (a) Mumm, O.; Hesse, H.; Volquartz, H. Ber. 1915, 48, 379.
    • The reaction described here is a special instance of a Mumm rearrangement which involves a 1,3-O→N acyl transfer not in the formimidate series. However, the formimidate context reported here renders this reaction unique. For literature access to the Mumm reaction, see: (a) Mumm, O.; Hesse, H.; Volquartz, H. Ber. 1915, 48, 379.
  • 13
    • 53549135148 scopus 로고    scopus 로고
    • In our first paper in this series ref 1, we described a direct pathway to 4, via a formal cycloaddition pathway, which does not pass through 3. In this paper, we focus on the presumed pathway from 3 to 4. However, involvement of the direct cycloaddition pathway to reach 4 is not ruled out
    • In our first paper in this series (ref 1), we described a direct pathway to 4, via a formal cycloaddition pathway, which does not pass through 3. In this paper, we focus on the presumed pathway from 3 to 4. However, involvement of the direct cycloaddition pathway to reach 4 is not ruled out.
  • 18
    • 34249088907 scopus 로고    scopus 로고
    • The structure was presumed on the basis of its infrared spectrum, (e) Isaka, M.; Boonkhao, B.; Rachtawee, P.; Auncharoen, P. J. Nat. Prod. 2007, 70,
    • The structure was presumed on the basis of its infrared spectrum, (e) Isaka, M.; Boonkhao, B.; Rachtawee, P.; Auncharoen, P. J. Nat. Prod. 2007, 70,
  • 19
    • 84971086544 scopus 로고
    • For cyclic structures of formimidate-carboxylate mixed anhydride, see: f
    • For cyclic structures of formimidate-carboxylate mixed anhydride, see: (f) Black, D. S. C.; Boscacci, A. B. Aus. J. Chem. 1977, 30, 1109.
    • (1977) Aus. J. Chem , vol.30 , pp. 1109
    • Black, D.S.C.1    Boscacci, A.B.2
  • 23
    • 45749083425 scopus 로고    scopus 로고
    • In some instances, spectroscopic suggestion of such an intermediate has been described, for example: (a) Hou, J-L.; Ajami, D.; Rebek, J., Jr J. Am. Chem. Soc. 2008, 130, 7810.
    • In some instances, spectroscopic suggestion of such an intermediate has been described, for example: (a) Hou, J-L.; Ajami, D.; Rebek, J., Jr J. Am. Chem. Soc. 2008, 130, 7810.
  • 25
    • 84978981855 scopus 로고    scopus 로고
    • Greater progress in characterization has been achieved with related mixed anhydrides which are not in the formimidate series, cf. inter alia: (a) Kawasaki, K, Tsumura, S, Katsuki, T. Synlett. 1995, 12, 1245
    • Greater progress in characterization has been achieved with related mixed anhydrides which are not in the formimidate series, cf. inter alia: (a) Kawasaki, K.; Tsumura, S.; Katsuki, T. Synlett. 1995, 12, 1245.
  • 28
    • 53549129149 scopus 로고    scopus 로고
    • -1 for the alleged mixed anhydride 7.
    • -1 for the alleged mixed anhydride 7.
  • 29
    • 53549111268 scopus 로고    scopus 로고
    • Typical IR absorptions reported for a nonformimidate mixed anhydride of the type 7 are ca. 1710-1660 cm-1; see ref 7
    • -1; see ref 7.
  • 30
    • 0000443935 scopus 로고
    • The NMR spectrum of the diffraction worthy crystal is the same as that of the bulk material. For a crystal structure based on a hydrogen-bonded complex between two small molecules, see
    • The NMR spectrum of the diffraction worthy crystal is the same as that of the bulk material. For a crystal structure based on a hydrogen-bonded complex between two "small molecules", see: Leiserowitz, L.; Nader, F. Acta Crystallogr. 1977, B33, 2719.
    • (1977) Acta Crystallogr , vol.B33 , pp. 2719
    • Leiserowitz, L.1    Nader, F.2
  • 44
    • 53549135687 scopus 로고    scopus 로고
    • Microwave heating of Gloede's product (purported 15) in chloroform again failed to produce the desired N-formylamide.
    • Microwave heating of Gloede's product (purported 15) in chloroform again failed to produce the desired N-formylamide.
  • 45
    • 53549103793 scopus 로고    scopus 로고
    • It should be noted that the elemental analysis, N, 10.45, ref 3b of Gloede's product 15 (calcd, N, 10.14) fits better for compound 17 (calcd, N, 10.33) than that concluded by Gloede. As reported by the authors, the claimed 15 does not react with methanol under reflux conditions
    • It should be noted that the elemental analysis, "%N = 10.45," (ref 3b) of Gloede's product 15 (calcd % N = 10.14) fits better for compound 17 (calcd. %N = 10.33) than that concluded by Gloede. As reported by the authors, the claimed 15 does not react with methanol under reflux conditions.
  • 46
    • 0010519267 scopus 로고    scopus 로고
    • Authentic 1,3-dicyclohexylamidine (18) was prepared according to a known procedure: Taylor, E. C.; Ehrhart, W. A. J. Org. Chem. 1963, 28, 1108.
    • Authentic 1,3-dicyclohexylamidine (18) was prepared according to a known procedure: Taylor, E. C.; Ehrhart, W. A. J. Org. Chem. 1963, 28, 1108.
  • 50
    • 46549104725 scopus 로고    scopus 로고
    • This concept was suggested to account for the small amount of amide formation at room temperature; see ref 1. For cyclization examples that do not follow Baldwin's rule, see: Astudillo, M. E. A, Chokotho, N. C. J, Jarvis, T. C, Johnson, C. D, Lewis, C. C, McDonnel, P. D. Tetrahedron 1985, 41, 5919
    • This concept was suggested to account for the small amount of amide formation at room temperature; see ref 1. For cyclization examples that do not follow Baldwin's rule, see: Astudillo, M. E. A.; Chokotho, N. C. J.; Jarvis, T. C.; Johnson, C. D.; Lewis, C. C.; McDonnel, P. D. Tetrahedron 1985, 41, 5919.
  • 51
    • 53549105749 scopus 로고    scopus 로고
    • Both isonitriles 25 and 27 were prepared in racemic form.
    • Both isonitriles 25 and 27 were prepared in racemic form.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.