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

By Alan R. Katritzky

This quantity within the sequence summarizes the various tools of the synthesis of heterocycles from azadienes with sections overlaying 1-azadienes, 2-azadienes, and 1,3-diazadienes. It covers the piperazine-2,5-diones and similar lactim ethers - accomplished evaluation of those hugely vital intermediates for the practise of a large choice of common items. The e-book explains how 1,2,4-Triazolo [1,5-a] pyrimidines are of specific value in images with different major program in prescription drugs and agrochemicals. It additionally stories tetramic acids, an importantgroup of common items displaying signifcant organic job, in addition to a few chemistry.

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In this context, Prato and Scorrano et al. were able to achieve the [4 + 21 cycloaddition of ethyl N-phenyl glyoxylate imines with dihydrofuran and indene leading to hexahydrofuro[3,2-c]- and tetrahydro-7H-indeno[2,l-c]quinolines,respectively, in moderate to good yields (88JHC 183 1). Similarly, tetrahydroquinoline derivatives were formed by [4 + 21 cycloaddition of 1,2-bis(trimethylsily- 207 208 E =C q M e Im = I-Imidazolyl SCHEME 48 209 44 [Sec. B JOSE BARLUENGA AND MIGUEL TOMAS C02Me Me$i, Me@C-C=CC-C02Me Meo2+x D CHzCCIz (R1= Ph) R' 2 10 211 (X = SiMe3) 212 (X = H) F02Me 'H 214 213 SCHEME 49 1oxy)cyclobutene and imines derived from aromatic aldehydes and aniline (84H355).

B poor 2-azadienes have been shown, reports dealing with electronically neutral 2-azadienes are scarcely found before the 1980s (84H355, 84JOC2691; 85JOC5678). On working in this particular field, we reported the first Diels-Alder reaction of simple neutral 2-azadienes 139 (Scheme 60). Treatment of aliphatic or aromatic aldehydes with substituted 2azadienes 139 at 60°C in the presence of catalytic amounts of boron trifluoride etherate resulted in the stereoselective formation of 1,3-0xazine cycloadducts 271 in 70-95% yield, which arise from an endo transition state (85CB3652).

Et 22 JOSE BARLUENGA AND MIGUEL TOMAS [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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