Advances in Heterocyclic Chemistry, Vol. 57 by Alan R. Katritzky

By Alan R. Katritzky

This quantity within the sequence summarizes the numerous equipment of the synthesis of heterocycles from azadienes with sections masking 1-azadienes, 2-azadienes, and 1,3-diazadienes. It covers the piperazine-2,5-diones and comparable lactim ethers - complete overview of those hugely vital intermediates for the guidance of a wide selection of normal items. The e-book explains how 1,2,4-Triazolo [1,5-a] pyrimidines are of specific significance in images with different major software in prescription drugs and agrochemicals. It additionally stories tetramic acids, an importantgroup of normal items exhibiting signifcant organic job, in addition to a few chemistry.

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36 [Sec. B JOSE BARLUENGA AND MIGUEL TOMAS vinylazadienes of this type, they have reported on the cyclization of Naryl(heteroary1) systems A (88JOC4654)and B (908474;92JOC929) as well as of N-vinyl derivatives C (88TL379)and D (9134175,91T6737). Representative examples by Saito and Motoki (92CC22)and Molina (91TL5379) leading to quinolines 173 and pyrido[2,3,4-de]quinazolines 177, respectively, are shown in Scheme 41. - R'N=C=O 25"C+ 170°C I ii Nx R1 *'"'" q7c02 II ii 174 P I1 175 /N N II - \ 'yN\ NHR' Rl il XH X 17 7 (X = NR2, 43-50 %) 176 (X = CR2R3: 69-70 %) SCHEME 41 Sec.

1. 36 [Sec. B JOSE BARLUENGA AND MIGUEL TOMAS vinylazadienes of this type, they have reported on the cyclization of Naryl(heteroary1) systems A (88JOC4654)and B (908474;92JOC929) as well as of N-vinyl derivatives C (88TL379)and D (9134175,91T6737). Representative examples by Saito and Motoki (92CC22)and Molina (91TL5379) leading to quinolines 173 and pyrido[2,3,4-de]quinazolines 177, respectively, are shown in Scheme 41. - R'N=C=O 25"C+ 170°C I ii Nx R1 *'"'" q7c02 II ii 174 P I1 175 /N N II - \ 'yN\ NHR' Rl il XH X 17 7 (X = NR2, 43-50 %) 176 (X = CR2R3: 69-70 %) SCHEME 41 Sec.

B On the contrary, while working in the synthesis of the alkaloid rubrolone, Boger and Zhu (91TL7643) have found 0-alkyl a$-unsaturated oximes 98 to participate as effective 41r components of an intramolecular Diels-Alder reaction with an electron-deficient dienophile. Thus, 98 was prepared from butane- 1,4-dioland heated in triisopropylbenzene to furnish 2-pyrindine derivatives 99 by virtue of in situ elimination of alcohol (Scheme 25). Among other leading workers in this field were Saegusa (81JA5250; 83TL2881; 86SC1073), Kametani (84TL4541; 85CC1159, 85H1097), and Dolle (88TL6349),who employed o-quinone methide imines, 2-trialkyloxysilyl-1-azabutadienes, and 1-dimethylamino-1-azabutadienes,respectively, as the reactive heterodienes in the intramolecular cycloaddition.

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