534572-15-1

Upstream product

• 287728-57-8 methyl 2-phenylspiro(cyclopropane-1',4-oxazoline)-5-carboxylate 
• 82979-45-1 methyl 2-chloro-2-cyclopropylideneacetate 
• 55-21-0 benzamide 

Downstream Products

• 534572-18-4 (7-TES-baccatin III)-13-yl (5R)-2-phenylspiro[cyclopropane-1',4-oxazoline]-5-carboxylate 
• 534572-16-2 (7-TES-baccatin III)-13-yl (5S)-2-phenylspiro[cyclopropane-1',4-oxazoline]-5-carboxylate 
• 1060757-46-1 N-(5-chloro-2-hydroxyphenyl)-5-phenyl-6-oxa-4-azaspiro[2.4]hept-4-ene-7-carboxamide 
• 534572-19-5 3'-(N-debenzoyl)-3'-dephenyl-3',3'-ethylene-2'-O-benzoyl-2'-epi-taxol 
• 534572-21-9 C₄₃H₄₉NO₁₄ 
• 534572-25-3 3'-dephenyl-3',3'-ethylene-2',7-epi-taxol 
• 534572-31-1 (baccatin III)-13-yl (5S)-2-phenylspiro[cyclopropane-1',4-oxazoline]-5-carboxylate 
• 534572-32-2 (baccatin III)-13-yl (5R)-2-phenylspiro[cyclopropane-1',4-oxazoline]-5-carboxylate 

Relevant academic research and scientific papers

A convenient access to variously substituted spiro[cyclopropane-1,4′- oxazoline]

Michael additions of carboxamides 2a-d under basic conditions onto methyl 2-chloro-2-cyclopropylideneacetate (1) with subsequent ring closure furnished the 4-spirocyclopropanated methyl oxazolinecarboxylates 3a-d (51-81%yields), from which the corresponding free carboxylic acids 4a-d were obtained by hydrolysis in excellent yield (89-93%). Coupling reactions of 4a-d with different o-hydroxyaniline derivatives in the presence of HOAt/EDC and 2,4,6-collidine gave the anilides 5 in good to very good yields (55-92%). The latter under Mitsunobu reaction conditions (Ph3P/DEAD) furnished the benzoxazole derivatives 6 (81-88%). The bromine substituent in the N-methylated 4-spirocyclopropanated 2-(bromophenyl)oxazoline-5-carboxanilides 8c,d were aminated with various secondary amines under Buchwald-Hartwig reaction conditions to give the 2-(aminophenyl)-oxazolinecarboxanilides 9 (12-90%). Suzuki cross-couplings of 8c with arene- and hetareneboronic acids provided the oxazolines with 2-biaryl substituents 10-13 (65-90%). Wiley-VCH Verlag GmbH & Co. KGaA, 2008.