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Volumn 25, Issue 5-6, 2006, Pages 509-518

Microwave-assisted Dimroth rearrangement of thiazines to dihydropyrimidinethiones: Synthetic and mechanistic aspects

Author keywords

Continuous flow; Density functional theory calculations; Differential scanning calorimetry; Dimroth rearrangement; Heterocycles; Microwave irradiation

Indexed keywords

CALORIMETERS; COMPUTATION THEORY; DENSITY FUNCTIONAL THEORY; DIFFERENTIAL SCANNING CALORIMETRY; IRRADIATION; ORGANIC SOLVENTS; REACTION INTERMEDIATES;

EID: 33745787244     PISSN: 1611020X     EISSN: 16110218     Source Type: Journal    
DOI: 10.1002/qsar.200540210     Document Type: Article
Times cited : (58)

References (58)
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    • B. S Thyagarajan (Ed.), Wiley-Interscience, New York
    • c) D. J. Brown in "Mechanisms of Molecular Migrations", Vol. 1, B. S Thyagarajan (Ed.), Wiley-Interscience, New York, 1968, pp. 209-245.
    • (1968) Mechanisms of Molecular Migrations , vol.1 , pp. 209-245
    • Brown, D.J.1
  • 27
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    • and references therein
    • c) R. V. A. Orru, M. de Greef, Synthesis 2003, 1471-1499, and references therein.
    • (2003) Synthesis , pp. 1471-1499
    • Orru, R.V.A.1    De Greef, M.2
  • 28
    • 0027205552 scopus 로고
    • DHPMs of type 2 are typically prepared by Biginelli multicomponent condensation. This approach, however, invariably leads to N1-substituted DHPM, and not to N3-substituted analogs. For reviews, see: a) C. O. Kappe, Tetrahedron, 1993, 49, 6937-6963.
    • (1993) Tetrahedron , vol.49 , pp. 6937-6963
    • Kappe, C.O.1
  • 31
    • 84890740903 scopus 로고    scopus 로고
    • J. Zhu, H. Bienaymé (Eds), Wiley-VCH, Weinheim
    • d) C. O. Kappe, in "Multicomponent Reactions", J. Zhu, H. Bienaymé (Eds), Wiley-VCH, Weinheim, 2005, pp. 95-120.
    • (2005) Multicomponent Reactions , pp. 95-120
    • Kappe, C.O.1
  • 34
    • 85192505274 scopus 로고    scopus 로고
    • note
    • One of the main limitations of microwave scale-up technology is the restricted penetration depth of microwave irradiation into absorbing materials, i.e., solvents or reaction mixtures. At the operating frequency of 2.45 GHz, the penetration depth is in the order of a few centimeters, depending on the dielectric properties of the medium. This means that the microwave power density inside a large batch reactor (> 1 L of volume) may only be a small fraction of the density on the surface. Therefore, solvents or reagents in the center of the reaction vessel are heated by convection and not by direct "in-core" microwave dielectric heating. This physical limitation is one of the main reasons for the development of continuous flow reactors, where the reaction mixture is passed through a relatively small microwave heated flow cell, avoiding penetration depth problems.
  • 41
    • 85192504430 scopus 로고    scopus 로고
    • note
    • For a recently reported flow-cell similar to the one depicted in Figure 2 filled with sand, see Ref. [15a].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.