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

By Alan R. Katritzky

This quantity within the sequence summarizes the various equipment 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 comparable lactim ethers - entire assessment of those hugely very important intermediates for the coaching of a wide selection of normal items. The publication 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 experiences tetramic acids, an importantgroup of normal items displaying signifcant organic job, in addition to a few chemistry.

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3-butenyl 193 195 196 194 (47-92 %) 197 19 8 (67-88 %Ib) R3=Ar,H SCHEME 45 Further work has been carried out by Ghosez (88TL3799, 88TL4573, 88TL6115; 89TL5887, 89TL5891) and others (79CL187; 87CB657, 87HCA1255; 88TL4401). Moreover, the cycloaddition reaction of 2azadiene 202 (Scheme 47) has been employed as the key step in the synthesis of alkaloid amphimedine 204 reported by Echavarren and Stille (88JA4051) and of marine antibiotic mimosamycin 205 carried out by McKillop and Brown (87SC657). Recently, Gouverneur and Ghosez (91TL5349) have described the asymmetric amination of carboxylic acids for synthesis of enantiomerically pure amino acids 206 via the Diels-Alder reaction of 202 with chiral nitroso dienophiles, as outlined at the bottom of Scheme 47.

Moreover, Komatsu et al. isolated thiazoles 142 on reaction of simple 2-azadienes 141 with sulfur dichloride (83PS119) (Scheme 35). However, vinyl isocyanates have been nicely demonstrated by the Rigby group to be particularly useful intermediates in synthesis of pyrroli- . 4 R 1 KCN 'YcN MeOH X=C@Me X X 137 136 R2 = Ph R3 = Me R2-R3 =(CH2)4 R4 = H, Me R5 = Ph. Me, COMe x = CN, COzMe R' = Morpholino ~ CN 138 R2 = Ph R3 = Me R2-R3 = (CH2)4 SCHEME 34 Sec. A] SYNTHESIS OF HETEROCYCLES FROM AZADIENES 31 R' R2 140 139 142 141 R' = k ,C-CrjH11 R2 = Me, Et, Pr R' = Ph,CHMe2 SCHEME 35 none derivatives (91JA8975) (Scheme 36).

On the other hand, consecutive aza-Wittig reaction of bis(iminophosph0rane) 174 with one molar equivalent of isocyanate or ketene and then with a second equivalent of isocyanate yielded bis-cumulenes 175, which were converted into pyrido[2,3,4-de]quinazoline derivatives 177 upon heating at 170°C; the reaction course is explained in terms of pyrido annelation of 175 to 176 via electrocyclic ring closure of the styryl carbodiimide portion and intramolecular amination. 2 . From (5 + I] Fragments The already-mentioned 2-azadienes 136 have become suitable starting materials for the synthesis of six-membered heterocycles as a five-atom fragment (Scheme 42).

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