Chemistry of benzo b thiophenes

Iddon, B., Scrowston, R. M., Recent Advances in the Chemistry of Benzo[b]-thiophenes, 11, 177. 

As in the case of the furopyridines (Section 3.17.2.1.1), there are six thienopyridine systems (Scheme 59) those derived from benzo[Z> ]thiophene (258-261) and those that are analogs of benzo[c]thiophene (262-264). The chemistry of thienopyridines has previously been reviewed both as an overview (72IJS(B)(7)309) and in a detailed manner (77AHC(2l)65, 81H(15)1285). The latter article presents a correlation of the chemistries of thieno[2,3-/ ]pyridine and thieno[3,2-6]pyridine with those of benzo[6]thiophene and quinoline. 

The pyrolysis properties of four model compounds were examined. Their molecular structures are shown in Table II. The three and four-ring molecules, containing a benzo [b] thiophenic unit were synthesized by Dr. Cagniant (L.S.C.O., Metz University). A polycyclohexanesulfide is an aliphatic sulfide synthesized by Dr. N. Spassky (Laboratory of Macromolecular Chemistry, Paris VI University). Polymeric aromatic sulfide was represented by a polybenzosulfide provided by Philips Petroleum. 

Recent advances in the chemistry of benzo[/ ]thiophenes , Iddon, B. and Scrowston,... 

A review entitled thiophenes from Viktor Meyer to Poly (thiophene) some reactions and synthesis was published in a special issue of Phosphorus, Sulfur and the related elements (13PS287). Over 80 reaction schemes are presented outlining important discoveries in the chemistry of thiophenes. Another review generalized published data on the reactions of 4-(2-R-aryl)-1,2,3-thia- and selenadiazoles (13RJOC479). Special emphasis on the use of these selenadiazole for the synthesis of 1-benzothiophenes, 1-benzosele-ophenes, and their more complex derivatives was presented. A recent review on recent advances in the use of the Wfllgerodt-Kindler reaction in thiophene syntheses appeared this year (13CSV7870). Extensive reviews on selenium and tellurium chemistry from small molecules to biomolecules and materials (B-13M001) as well as data on the synthesis, reactions, crystal structures, and spectral characteristics of benzo[b]tellurophene, dibenzo[b,d]... 

This, the eleventh volume of Advances in Heterocyclic Chemistry, includes surveys of the chemistry of the following groups of heterocyclic compounds benzo[6]thiophenes (B. Iddon and ft. M. Scrow-ston), naphthyridines (W. W. Paudler and T. J. Kress), and quinu-clidines (L, N. Yakhontov). In addition, R. A. Jones covers the application of physical methods to pyrrole chemistry and a very topical subject, the photochemistry of heterocycles, is reviewed by S. T. Reid. 

Volume 14 of this serial publication comprises six chapters of which four deal with general accounts of ring systems benzisothiazoles (M. Davis), 1,2-dihydroisoquinolines (S. F. Dyke), benzo[c]thiophenes (B. Iddon), and pyrazines (G. W. H. Cheeseman and E. S. G. Werstiuk). One chapter updates a previous review in this series and is concerned with the rapidly expanding chemistry of mononuclear isothiazoles (K. R. H. Wooldridge). The remaining chapter (O. Meth-Cohn and H. Suschitzky) deals with the cyclizations of ortho-substituted f-anilines. 

Dihydrobenzo[c]thiophene (Section III,A) is also known as 1,3-dihydroisothianaphthene, 2-thiaindane, o-xylylene sulfide (commonly used), thiophthalan, 3,4-benzothiacyclopentane, and 3,4-benzo-2,5-dihydrothiophene. In this case we have used the first-mentioned name throughout other problems of nomenclature are discussed as they arise. Since I,3-dihydrobenzo[c]thiophenes are important intermediates in this field, their chemistry is discussed in detail. With other derivatives such as 2-thiophthalide (Section VII, A) and phthalic thioanhydride (Section VII, B), which may be regarded as l,3-dihydrobenzo[c]thiophen-l-one and 1,3-dihydro-benzo[c]thiophen-l,3-dione, respectively, our coverage of the literature may be incomplete, since we have only included references which arose directly or indirectly (i.e., as cross references) by searching benzo[c]thiophene or equivalent terms in CA. 

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