Chemistry

Advances in Heterocyclic Chemistry, Vol. 26 by A.R. Katritzky, A.J. Boulton (Eds.)

By A.R. Katritzky, A.J. Boulton (Eds.)

(from preface)Volume 26 comprises 3 chapters. C.A.Ramsden experiences heterocy-clic betaines derived from 6-membered heteroaromatic earrings. those compounds were intensively studied during the last 10 years and feature now not formerly been comprehensively reviewed. O. Meth-Cohn and B. Tarnowski summarize the chemistry of the thiocoumarins, a a little bit ignored crew of heterocycles. ultimately, W. Friedrichsen has reviewed the chemistry of the benzo[r]furans which, in contrast to the aza and thia analogs, haven't formerly been thought of during this sequence. the following back we now have a gaggle of compounds the chemistry of which has complicated significantly during the last decade.

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5”C, which was originally assumed to be 1-methylcinnolin-4-one (234; R’=Me, R 2 = R 3 = R 4 = R 5 = R 6 = H ) l s 3 but later reformulated as 2-methylcinnolinium-4-olate (233; R’ = Me, R2 = R3 = R4 = R 5 = R6 = H ) on the basis that reduction with lithium aluminum hydride gave 1,2,3,4-tetrahydr0-2-methylcinnoline(235). ’ 5 4 A series of detailed studies by Ames and co-workers’ 54-166 ha ve demonstrated that alkylation ’ IS* A. Padwa, P. Sackman, E. Shefter. and E. Vega, J . C. , Chem. , 680 (1972).

Perkin I , 305 (1975). Sec. IILB] 31 HETEROCYCLIC BETAINES 0 1 0 SCHEME7. Reagents: i, ion-exchange resin; ii, Et,N; iii, hv; iv, AT; v, RiRZC=CH2; vi, R ' C z C R ' ; vii, EtO,CN=NCO,Et; viii, Mel: ix, Ag,O or NaHCO,. Acetylenes and diethyl azodicarboxylate give similar adducts (173 and 174)(Scheme 7). Menschutkin methylation of 172 gives the methiodides (175) which undergo Hofmann elimination to 2-dimethylamino-6,7-benzotropones (177) (Scheme 7). The benzocycloheptadienones (176) are not Dennis, A .

L. Stafford, J . Chern. ,1579(1959). J. P. Phillips and R. W. Keown, J . Am. Chem. 73, 5483 (1951). Sec. B] HETEROCYCLIC BETAINES 35 ( 194) exo-anti Derivatives of this system (191) have not been isolated. The parent molecule (191; R = H) and a methyl derivative (191; R = Me) have been generated in solution but dimerization occurs rapidly. Thus, cyclodehydration of (benzy1thio)acetic acid (PhCH,SCH,CO,H) gives isothiochroman-Cone (192; R = H) which with triphenylmethyl perchlorate gives 4-hydroxy-2benzothiopyrylium perchlorate (193; R = H).

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