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Download Advances in Carbohydrate Chemistry, Vol. 13 by M. L. (editor) Wolfrom PDF

By M. L. (editor) Wolfrom

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Microwave-assisted synthesis of heterocycles

This e-book is quantity I of a brand new sequence via Springer entitled subject matters in Heterocyclic Chemistry. at the present, there are six such monographs during this sequence, the general scope of that is to hide "current developments in heterocyclic chemistry". Given the significance of heterocylic ordinary items and heterocyclic scaffolds within the realm of medicinal chemistry and drug discovery, an up-todate sequence in this topic is easily warranted, and a survey of the hot impression of microwave-assisted synthesis in this venerable box is either well timed and wanted.

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2846 (1949). (65) J . C. , 12, 35 (1957). (66) W. Schnelle and B. Tollens, A n n . 61 (1892). ^^ According to these authors, in the idealized, planar-ring structure of cyclepentane (XI), there is a substantial strain resulting from ten bond-oppositions; introduction of a carbonyl group, which assumes a staggered conformation (XII) with respect to the neighboring bonds, stabilizes the ring by XI (10-bond opposition; 10 Kcal. strain) XI1 (6-bond opposition; 6 Kcal. strain) diminishing the number of bond oppositions to six.

Cyclic (XXXV) or of an acyclic (XXXIX) carbonium ion-with rapid, subsequent stages, as shown in Fig. 1. At present, there is no general or conclusive proof in favor either of the cyclic or of the acyclic pathways. However, there is much circumstantial evidence indicating the cleavage of the oxygen ring and the formation of an acyclic intermediate, particularly for the reactions involving the interconversion of furanosides and pyranosides. This mechanism accounts for the formation of ethyl l-deoxy-lthio-a-D-glucopyranoside (XLVI), ethyl 1-deoxy-1-thio-P-D-glucopyranoside (XLVII), the reducing sugar (XLIV), and a lesser amount of ethyl 1-deoxy-1-thio-0-D-glucofuranoside(XLV) from the hydrolysis of ethyl 1-deoxy-1-thio-a-D-glucofuranoside (XLIII) as described previously (see page 31).

M. Lowry, J. Chem. ,83, 1314 (1903); 86,1551 (1904). (135) G. F. Smith and T. M. Lowry, J. Chem. , 665 (1929). (136) T. M. Lowry, J. Chem. ,127, 1371 (1925). (137) H. Hudson, M. L. Wolfrom and T. M. Lowry, J. Chem. ,1179 (1933). (138) K. Goto and T. Titani, Bull. Chem. Japan, 16, 403 (1941). (139) S. M. Cantor and Q. P. Peniston, J. Am. Chem. , 62,2113 (1940). (140) J. M. Los, L. B. Simpson and K. Wiesner, J . A m . Chem. , 78,1564 (1956). (141) W. G. Overend, A. R . Peacocke and J. B. Smith, Chem.

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