γ′[C(sp3)–H] functionalization of ynones is described. Nucleophilicaddition of an organophosphine to the designed ynones generates heteroaryl-based ortho-quinodimethanes (oQDMs), which undergo carbocyclization to provide a variety of cyclopenta-fused benzothiophenes. This approach also constitutes an unusual organophosphine-catalyzed intramolecular hydroalkylation of ynones. An efficient organocatalytic
摘要 描述了一种有效的有机催化方法,用于通过苯并噻吩的γ'[C(sp 3)–H]官能化苯并噻吩环化[ b ] 。将有机膦亲核地加到设计的炔酮上会生成基于杂芳基的邻二醌二甲烷(oQDMs),将其进行碳环化反应以提供各种环戊基稠合的苯并噻吩。该方法也构成了异常的有机膦催化的炔酮分子内氢烷基化反应。 描述了一种有效的有机催化方法,用于通过苯并噻吩的γ'[C(sp 3)–H]官能化苯并噻吩环化[ b ] 。将有机膦亲核地加到设计的炔酮上会生成基于杂芳基的邻二醌二甲烷(oQDMs),将其进行碳环化反应以提供各种环戊基稠合的苯并噻吩。该方法也构成了异常的有机膦催化的炔酮分子内氢烷基化反应。
Synthesis of 1,2,3-Trisubstituted Cyclopentannulated Benzothiophenes through an Acid-Mediated, Solvent-Free, One-Pot Domino Process
作者:Bishnupada Satpathi、Seema Dhiman、S. S. V. Ramasastry
DOI:10.1002/ejoc.201400008
日期:2014.4
The synthesis of 1,2,3-trisubstituted cyclopenta[b]thiophenes was achieved through a Bronsted acid mediated dominoprocess under solvent-free conditions. In this one-potprocess, benzothienylation of 1,3-dicarbonyls follows an intramolecular aldol-type reaction leading to the generation of functionalized and highly substituted annulated benzothiophenes. This class of compounds find potential applications