Abstract
Decomposition of the diazonium chloride from N-(o-aminobenzoyl)-N-methylbenzylamine led to the formation of 3-benzyl-3, 4-dihydrobenzo-triazin-4-one (8), N-benzoylbenzylamine (11), N-benzylphthalimidine (13) ando-diphenic acid N-methyl amide (14), the last one presumably through the intermediary, the expected dibenzazepinone 16. From the analogue, N-(o-aminobenzoyl)-4-methoxybenzyl amine (4), triazinone 10 and N-benzoyl-4-methoxybenzyl amine (12) were obtained. Application of Pschorr reaction to N-(o-aminobenzoyl)-N-methyl-β-(4-methoxyphenyl) ethyl amine (23) afforded 2-methoxy-7-methyl-5, 6, 7, 8- tetrahydrodibenzo (c, e) azocin-8-one (26), with an interesting conformation. From N-(o-aminophenylacetyl)-p-methoxyaniline were obtained under these conditions, indazole-3-carboxylic acidp-anisidide (35) and N-[2-(4-methoxyphenyl carbamoylmethyl) phenyl]-1-(p-methoxyphenyl) isatin-β-hydrazone (37). The structure of 37 was deduced from spectral data and hydrolysis to the acid 42. Diazotisation of N-(o-aminophenylacetyl)-1, 2, 3, 4-tetrahydroquinoline (47) led to the formation of tetrahydroquinoline (49) ando-hydroxyphenyl acetic acid (50) presumably through the salicylamide 48. A similar reaction on N-(o-aminophenylacetyl) tetrahydroisoquinoline (52) gave the benzofurandione hydrazone 55, besides tetrahydroisoquinoline. Oxindole 45 and benzofuranone 56 were likely precursors for 37 and 55 respectively. Salicylamides 5, 7, 24 and 34 were byproducts in the Pschorr reaction.
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Abdulina R N 1975Chem. Abst. 82 80652v
Abdusamatov A, Abduazimov Kh A and Yunusov S Yu 1969Chem. Abst. 71 12862 4 q
Becke F and Jagla E 1968 U S Patent 3 317 558 to BASFChem. Abst. 68 59327
Buveva-Ivanova L 1962Ber. 95 1348
DeTar D F 1957 inOrganic Reactions (New York: John Wiley)9 409
Francis S and Belleau B 1973Bio-organic Chem. 2 111;Chem. Abst. 78 120613
Franck B and Lubs H J 1969Liebigs Ann. der. chemie 720 131
Gadamer J, Oberlin M and Schoeler A 1925Arch. Pharm. 263 81
Govindachari T R and Arumugam N 1955J. Sci. Ind. Res. 14 250
Govindachari T R, Nagarajan K and Ramadas C V 1958J. Chem. Soc. 983
Hey D H and Turpin D G 1954aChem. Ind. 216 221
Hey D H and Turpin D G 1954bJ. Chem. Soc. 2471
Jeffs P W, Hansen J F and Brine G A 1975J. Org. Chem. 40 2883
Kametani Tet al 1971a J. Chem. Soc. C 590
Kametaniet al 1971b J. Chem. Soc. C 1800
Kotera Ket al 1968Chem. Abst. 68 105398t
Nagarajan K, Madhavan Pillai P and Bhute R S 1969Indian J. Chem. 7 848
Pschorr Ret al. 1896Ber. 29 496
Walling C 1957 inFree Radicals in Solutions (New York: John Wiley) p 278
Weisbach J A, Burns C, Macko E and Douglas B J 1963J. Med. Chem. 6 91
Wildman W C 1968 inAlkaloids ed. R H F Manske (New York: Academic Press)XI 348
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Dedicated to the memory of late Professor H Schmid of Zurich University.
Contribution No. 484 from CIBA-GEIGY Research Centre.
Presented before the Convention of Chemists, Bombay, October 28–November 1, 1971; Abstracts, p. 90.
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Nagarajan, K., Pillai, P.M., Goud, A.N. et al. Application of Pschorr reaction to N-(o-aminobenzoyl)-benzyl and phenethyl amines and to N-(o-aminophenylacetyl) anilines. Proc. Indian Acad. Sci. 86, 25–39 (1977). https://doi.org/10.1007/BF03046649
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DOI: https://doi.org/10.1007/BF03046649