Download e-book for iPad: Advances in Heterocyclic Chemistry, Vol. 51 by Alan R. Katritzky
By Alan R. Katritzky
(from preface)Volume fifty one of Advancesconsists of 3 chapters, V. V. Mezheritskii and V. V. Tkachenko (Rostov-on-Don, U.S.S.R.) assessment the synthesis of peri-annelated heterocycles, a wide and engaging category which has no longer formerly been handled in a scientific type. R. M. Acheson (Oxford, U.K.) offers the 1st special survey of l-hydroxypyrroles and their benzo derivatives, compounds which exhibit a fascinating and weird chemistry. eventually, B. A. Trofimov (Irkutsk, U.S.S.R.) describes the mini-fold preparative hazard for pyrroles from ketoximes and acetylenes, a response found by means of Trofimov and built via him right into a most vital access into pyrrole chemistry.Volume fifty one must have been an ''Index Volume,'' and certainly the indices have been already in a complicated degree, while severe sickness within the indexer's speedy kin avoided their inclusion during this quantity. they are going to seem in a later quantity.
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Extra info for Advances in Heterocyclic Chemistry, Vol. 51
Construction of benzo[cd]indole nucleus from naphthaloimide derivatives. The general principle of synthesizing naphthostyryl and its derivatives 174 is based on oxidation of naphthaloimides 178 in the Hofmann reaction [06CB(42)2336; lOCB439; 1 lBSF86; 22HCA560; 54MI1; 55ZOB2485; 57MIl; 61MI11 or on rearrangement of N-dinitrophenyloxy (74ZOR2232; 77ZOR2194) and N-acyloxy- [%MI1 ;66JCS(C)523 ;70ZOR1480; 72ZOR165; 73ZOR171; 75GEP2417789; 76ZOR1057, 76ZOR1787; 77GEP2628653; 81TH1,81ZOR1013) naphthaloimides 18Ob-e by the action of bases (alkali metal hydroxides, alcoholates, and amines).
V . TKACHENKO CI R@ CI +HO/Q \ H02C R CQH gNR b. Naphtho[bc]thiupyruns. The principles of heterocyclic construction of naphtho[bc]thiapyrans are the same as those for naphtho[bc]pyrans. The general pathway to 3-acetoxy derivatives of naphtho[bclthiapyran 301 consists of the synthesis of peri-carboxynaphthothia-acetic acids 300 from naphthothialactones 76. The acids 300 are then cyclized into desired compounds 301 in acetic anhydride with sodium acetate [ 12- (76) ( 300) (301) LA(388)l; 68M2VK462; 70KGS1031; 73KGS1034).
V. MEZHERITSKII AND V. V. TKACHENKO [Sec. B The heterocyclization of peri-aminonaphthoic acids is significantly hindered if the other two carbon peri-atoms are incorporated into the fivemembered ring. However, on lengthy heating, the cyclization occurs under fairly severe conditions. Thus, boiling 4,5-aminoacenaphthoic acid or 5-amino-6-carboxynaphthostyrylin acetic anhydride gives rise to compounds 140 (68DOK852) or 141 (75ZOR1731), and heating 6-bromo5-carboxynaphthostyryl with aryl amines leads to bis-lactam 142 [%I JC(B)377].
Advances in Heterocyclic Chemistry, Vol. 51 by Alan R. Katritzky