ADVANCES IN HETEROCYCLIC CHEMISTRY V51, Volume 51 by Alan R. Katritzky

By Alan R. Katritzky

Meant for natural chemists, this quantity follows the layout of past volumes and offers up to date info on chosen components of heterocyclic chemistry.

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The formation of benzo[cd]indolium cations l31-133, which are different in terms of subsituents at the nitrogen atom or in position 2, occurs on briefly heating azomethine perchlorates 130 in acetic anhydride (84ZOR225; 85ZOR1941). The course of reaction and the character of the final products are determined by electronic effects of substituents at the aryl ring (Ar) of Nprotonated azomethine 130. The most interesting is the reaction leading to 2-styrylbenzo[cd]indolium salts 132; the formation of which can be represented as the result of a rearrangement of intermediate l34.

B) 23 PERI-ANNELATED HETEROCYCLES 8-Amino-Cmethoxy-I -methoxymethylnaphthalene 120, obtained from the chloromethyl derivative 111, is transformed into azide 121. The reduction of methyl or phenyl 8-nitro-1-naphthyl ketones by hydrogen and platinum dioxide or by iron in acetic acid leads to a mixture of products (59M634). If acenaphthene derivatives have a bimethylene bridge “pulling” together peri-positions, the closure of the second five-membered ring is hindered, and in this case, the isolation of peri-aminoacenaphthalene ketones l23 (662013148; 68ZOR2002) formed on reduction of peri-nitro ketones 122 (20CB289;25CB2239; 62MII; 64BSF646; 68ZOR2002) is possible.

On gas phase photolysis of naphtho[bc]0 -so2 ~ \ / H0 A s03~ ~ / HzN z SojH L H N-502 & p (247) (246) thiete S,S-dioxide, naphtho[cd]oxathiol S-oxide 248 was found among the other products (67LA96). (248) Formation of an N-0 bond, together with the isooxazole ring closure, proceeds on thermal decomposition of 1-azidoanthraquinonesand leads to & Sec. C] PERI-ANNELATED HETEROCYCLES 45 isooxazoleanthrones 249 (83MI1; 84ZOR2452). The unusual transfor- mation of I-nitroso-2-isopropylanthraquinone250 under strongly acidic conditions gives rise to isooxazoleanthrone 251 (68DOK1099).

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