By Alan Katritzky
The definitive serial within the box - on account that 1960. * offers updated fabric on a quick becoming and hugely topical topic region * comprises the newest study masking a large choice of heterocyclic themes * Written via prime experts and designed as a guide for college students and and educational researchers.
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Extra info for Advances in Heterocyclic Chemistry, Vol. 95
With 1-(3-oxopyrazol-4-yl)-3-substituted Thioureas . . . . . . . . . X. Solvolysis . . . . . . . . . . . . . . . . . . . . . . . . . A. Of Carbonyl and Arylsulfonylpyrazol-3-ones . . . . . . . . . . . B. Of 4-(iminophenylmethyl or phenylaminomethylene)pyrazol-3-ones . . . C. Of (5-oxopyrazol-3-yl)acetamide or 4,4-(dimorpholin-4-yl)pyrazol-3-one . . D. Of 4-(ethoxycarbonylmethyl)pyrazol-3-ones . . . . . . . . . . . . XI. Rearrangement .
The strongly nucleophilic primary amino group of pyrazol-3-ones 49a,b (Scheme 13) reacted under mild conditions with chloroacetyl chloride or bromide, 38 GEORGE VARVOUNIS ET AL. [Sec. A H S N O N O N Ph DIPEA NH2 O N N (54) (53) Cl + (51) S Ph + DMF O S H (52) (51) O S N O O N N Ph (55) H O + (51) RCOCl + R DMF (31) NH3 / MeOH O R N O (53) (51) H R N O N + N O N N Ph Ph (56) (57) SO3H (59) (a) R = Me (b) R = C6H11 (c) R = Ph (d) R = 4-n-PrC6H4 (e) R = 4-t-BuC6H4 (f) R = 4-n-BuOC6H4 (g) R = 4-CNC6H4 (h) R = 3-F-5-CF3C6H4 NH3 H NH2 N O N N O3S (58) Ph (60) Scheme 14 or with acetic anhydride to give 2-(3-oxopyrazol-2-yl) amides 50c–f.
A] 39 PYRAZOL-3-ONES. PART III varying conditions of temperature, solvents, substrate/reactant ratios, organic bases and use of carboxylic acid esters instead of acid chlorides, LC-MS analysis of the reaction mixture indicated the presence of starting amine 51, and acid chloride 52, the desired 4-N-acylpyrazol-3-one 54, and bis-acylated product 55. This problem was circumvented by utilizing a sequence of functionalized polymers serving both as stoichiometric reagents and puriﬁcation media. The method developed involved initially treating pyrazol-3-one 51 with acid chloride 31 in tetrahydrofuran in the presence of polymer-supported Hunig’s base.
Advances in Heterocyclic Chemistry, Vol. 95 by Alan Katritzky