Synthesis of functionalized 2H-1-benzopyrans by DBU-catalyzed reactions of salicylic aldehydes with allenic ketones and esters.

[reaction: see text] DBU-catalyzed reactions of salicylic aldehydes with 3-methylpenta-3,4-dien-2-one, 3-benzylpenta-3,4-dien-2-one, or ethyl 2-methylbuta-2,3-dienoate gave the corresponding functionalized 2H-1-chromenes in good to excellent yields and good diastereoselectivities in some cases in DMSO, respectively.

[1]  M. Shi,et al.  DABCO-catalyzed reaction of allenic esters and ketones with salicyl N-tosylimines: synthesis of highly functionalized chromenes. , 2005, Organic letters.

[2]  P. T. Kaye,et al.  A Convenient Baylis-Hillman Synthesis of 3-Substituted 2H-1-Benzothiopyrans , 2004 .

[3]  S. Bräse,et al.  Base‐Catalyzed Condensation of 2‐Hydroxybenzaldehydes with α,β‐Unsaturated Aldehydes – Scope and Limitations , 2005 .

[4]  O. Kwon,et al.  Phosphine-catalyzed synthesis of 1,3-dioxan-4-ylidenes. , 2005, Organic letters.

[5]  P. T. Kaye,et al.  Application of Baylis–Hillman methodology in a chemoselective synthesis of 3-acyl-2H-1-chromenes , 2000 .

[6]  P. T. Kaye,et al.  A Convenient and Improved BaylisHillman Synthesis of 3-Substituted 2H-1-Benzopyran-2-ones. , 2002 .

[7]  P. T. Kaye,et al.  A convenient general synthesis of 3-substituted 2H-chromene derivatives , 2002 .

[8]  Hisanori Horita,et al.  A New Preparative Method of 2,2-Dimethyl-2H-chromenes , 1982 .

[9]  B. Trost,et al.  A Catalytic Enantioselective Approach to Chromans and Chromanols. A Total Synthesis of (−)-Calanolides A and B and the Vitamin E Nucleus , 1998 .

[10]  P. T. Kaye,et al.  Application of Baylis–Hillman methodology in a novel synthesis of quinoline derivatives , 1998 .

[11]  Jae Nyoung Kim,et al.  Synthesis of 2,3,4,4a-Tetrahydroxanthen-1-ones and 3,3a-Dihydro-2H-cyclopenta[b]chromen-1-ones from the Reaction of Salicylaldehydes and 2-Cyclohexen-1-one and 2-Cyclopenten-1-one , 2003 .

[12]  P. T. Kaye,et al.  Does the DABCO-catalysed reaction of 2-hydroxybenzaldehydes with methyl acrylate follow a Baylis-Hillman pathway? , 2003, Organic & biomolecular chemistry.

[13]  S. Bräse,et al.  A short, atom-economical entry to tetrahydroxanthenones. , 2004, Angewandte Chemie.

[14]  P. T. Kaye,et al.  Dabco-Catalysed Reactions of Salicylaldehydes with Acrylate Derivatives , 1996 .

[15]  Y. Kawase,et al.  Reactions of salicylaldehyde with some conjugated olefins , 1992 .

[16]  P. T. Kaye,et al.  Efficient and Chemoselective Access to 3-(Chloromethyl)coumarins via Direct Cyclisation of Unprotected Baylis-Hillman Adducts , 2003 .

[17]  Xiyan Lu,et al.  Phosphine-catalyzed[3+2] cycloaddition reaction of methyl 2, 3-butadienoate and N-tosylimines. A novel approach to nitrogen heterocycles , 1997 .

[18]  T. Ohta,et al.  Discovery of insect anti-juvenile hormones in plants.?2U. , 1976, Science.