By G.W. Gribble, Thomas L. Gilchrist
This quantity of development in Heterocyclic Chemistry (PHC) is the 12th annual evaluation of the literature, overlaying the paintings released on many of the very important heterocyclic ring platforms in the course of 1999, with inclusions of prior fabric as acceptable. As in PHC-11, there also are 3 really good stories during this year's quantity. within the inaugural bankruptcy, Michael Groziak revitalizes the sector of boron heterocycles, a comparatively imprecise category of heterocycles, yet with a promising destiny. Heterocyclic phosphorus ylides are equally a bit recognized yet worthwhile classification of compounds and Alan Aitken and Tracy Massil have supplied a complete overview of them in bankruptcy 2. In bankruptcy three Jack Li discusses the remarkably flexible palladium chemistry in pyridine alkaloid synthesis.The next chapters care for fresh advances within the box of heterocyclic chemistry prepared by means of expanding ring dimension and with emphasis on synthesis and reactions.
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Additional info for A critical review of the 1999 literature preceded by three chapters on current heterocyclic topics
CO2E, S-" "SMe""------ S S'- -SEt 14 8 X 9X=O 10X=S 11 X = RN 13 12 Ph3P=C=C(OEt) 2 with CS2 gives the thietane ylide 12 which has a rather interesting reactivity. Upon heating at 100 ~ it rean'anges to 13 while treatment with methyl iodide results in loss of ethyl iodide to give 14 <79JCR(S)313>. The reaction of Ph3P=C=C=NPh with CO 2 takes an unexpected course: addition to give 15 is followed by ring-opening to give 16 which then undergoes ring closure to afford the azetidinedione system 17 <77TL3037>.
M e2Si--~, PR3 29 R = Me But2Si--~ si / PPh 3 Me2 32 31 30 R = Bu n The silicon-containing bis(ylides) 29 and 30 are formed by u'eatment of Me2SiC12 with an excess of R3P=CH 2 <70CB97> and reaction of Ph3P=CH 2 with But2SiC12 similarly affords 31 <87CB789>. The disilacyclobutane ylide 32 is formed by reaction of dilithiated Me3P=CH 2 with C1Me2SiCH2SiMe2C1 <78CB2696>. A similar approach has allowed preparation of a range of titanium-containing bis(ylides). Thus treatment of (Me2N)2TiC12 with 3 equivalents of Me3P=CH 2 gives compound 33 <77ZN(B)858> while reaction of (Et2N)3P=CH 2 and TiC14 in a 3:2 ratio gives 34 <86AG(E)574>.
Thereby, they prepared 3-indolylzinc reagent 14 from 3-bromo-l-(tert-butyldimethylsilyl)indole (13). Subsequent Negishi coupling of 14 with 2-halopyridine 11 gave 3-(2-pyridyl)indole 15. The Negishi adduct 15 was then further manipulated to a naturally occurring hexahydropyridine alkaloid, (+)-nordasycarpidone (16) <93TL5005, 96AQ62>. j t-B/Sl\u 2. N I /ZnCI 1~ ~ , , . Bu/Sl\ R m t-Bu ,;. 3 11 PdCI2(Ph3P)2, DIBAL THF, reflux 14 ,Q R2 R3 H X = CI or Br O 15 16 In their formal total synthesis of camptothecin (21), Murata and associates employed a Negishi reaction to establish the A, B and D ring linkage <97SL298>.
A critical review of the 1999 literature preceded by three chapters on current heterocyclic topics by G.W. Gribble, Thomas L. Gilchrist