Ahluwalia, V. K.; Sharma, Pooja; Goyal, Bindu, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1997, vol. 36, # 11, p. 1059 - 1061
Pyridinium N-Ylides and (Arylmethylene)azol-5-ones. Reaction Cascade Leading to an Unusual Spiroisoxazolinone Ring
摘要:
The reaction of a series of (arylmethylene)azol-5-ones with phenacylpyridinium salt 3 in glacial acetic acid/ammonium acetate mixture gives different results depending on the starting azolone. The isoxazol-5-ones 1 give the unusual spirans 6 in a reaction cascade involving Michael- and retro-Michael reactions, C-alkylation, aldol addition, and diastereospecific cyclization. The reaction performed with oxazol-5-ones 11 has shown that a literature re po rt has to he corrected since no oxazolopyridines 12 hut rather arylideneimidazol-5-ones 13 are produced. In the case of pyrazolin-5-ones 14, the unavoidable formation of bis-adducts 15 always prevents any other type of reaction. (C) 2000 Elsevier Science Ltd. All rights reserved.
Silica-bonded DABCO hydrogen sulfate ((SB-DABCO)HSO4): a new dual-interphase catalyst for the diversity-oriented pseudo-five-component synthesis of bis(pyrazolyl)methanes and novel 4-[bis(pyrazolyl)methane]phenylmethylene-bis(indole)s
and was successfully applied for the diversity-oriented synthesis of bis(pyrazolyl)methanes via a one-potpseudo-five-component condensation reaction. This approach provides a versatile range of available substrates and high diversity of desired products. Moreover, ((SB-DABCO)HSO4) was successfully applied for the synthesis of some novel [bis(pyrazolyl)methane]-bis(indole)s as more complex molecules