Regio- and π-Facial Selective Cycloadditions Involving 2-Phenyl-4-dimethylamino-1-thia-3-azabuta-1,3-diene and Allenic Esters: An Efficient Route to Novel 6-Alkylidene-6<i>H</i>-2-phenyl-5-ethoxycarbonyl-1,3-thiazines

Ishar, M. P. S.; Kapur, Ashish; Raj, Tilak; Girdhar, Navdeep K.; Kaur, Amritpal

doi:10.1055/s-2004-815995

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6 [4+2]-cycloadditions261 the Reactions Of 13-dienes With Al...1

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“…2-Phenyl-4-(dimethylamino)-1-thia-3-azabuta-1,3-diene 201 underwent regio- and stereoselective [4+2] cycloadditions with 2,3-allenoates 202 in CH 2 Cl 2 −benzene to afford 6-alkylidene-6 H -2-phenyl-5-ethoxycarbonyl-1,3-thiazines 204 (Scheme ) 45 …”

Section: 6 [4+2]-cycloadditions261 the Reactions Of 13-dienes With Al...mentioning

confidence: 99%

Some Typical Advances in the Synthetic Applications of Allenes

2005

Chem. Rev.

1,348

256

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In 1989, Kakiuchi et al. reported that under irridation propadiene can undergo [2+2]-cycloaddition with R,β-unsaturated cyclohexenones to afford methylene-cyclobutane-containing bicyclic products 1 (Scheme 1). 6 Shi et al. reported that under the catalysis of DABCO, N-tosylated imines 2 can undergo [2+2]cycloaddition with 2,3-butadienoate or 3,4-pentadien-2-one to afford azetidine derivatives 3. 7 The reaction proceeded via the nucleophilic addition of DABCO to the electron-deficient allene forming 4-and 5-type intermediate, which may undergo 1,2-addition with the imines to afford 6. Intramolecular conjugate Scheme 1

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Section: 6 [4+2]-cycloadditions261 the Reactions Of 13-dienes With Al...mentioning

confidence: 99%

Some Typical Advances in the Synthetic Applications of Allenes

2005

Chem. Rev.

1,348

256

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Regio‐ and π‐Facial Selective Cycloadditions Involving 2‐Phenyl‐4‐dimethylamino‐1‐thia‐3‐azabuta‐1,3‐diene and Allenic Esters: An Efficient Route to Novel 6‐Alkylidene‐6H‐2‐phenyl‐5‐ethoxycarbonyl‐1,3‐thiazines.

et al. 2004

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1,3-thiazines. -The 1-thia-3-aza-diene (I) undergoes a regio-and stereoselective [4 + 2] cycloaddition with allenes to yield cycloadducts (III)/(IV) and (VI) after elimination of dimethylamine. In the case of allenic ester (VII), the primary cycloadduct (VIII) is stable and can be isolated in high yield. -(ISHAR*, M. P. S.; KAPUR, A.; RAJ, T.; GIRDHAR, N. K.; KAUR, A.; Synthesis 2004, 5, 775-778; Dep. Pharm. Sci., Guru Nanak Dev Univ., Amritsar 143 005, India; Eng.) -Mais 32-179

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1,3-Thiazines and their Benzo Derivatives

Karodia

2008

Comprehensive Heterocyclic Chemistry III

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Regio- and π-Facial Selective Cycloadditions Involving 2-Phenyl-4-dimethylamino-1-thia-3-azabuta-1,3-diene and Allenic Esters: An Efficient Route to Novel 6-Alkylidene-6H-2-phenyl-5-ethoxycarbonyl-1,3-thiazines

Cited by 3 publications

References 20 publications

Some Typical Advances in the Synthetic Applications of Allenes

Some Typical Advances in the Synthetic Applications of Allenes

Regio‐ and π‐Facial Selective Cycloadditions Involving 2‐Phenyl‐4‐dimethylamino‐1‐thia‐3‐azabuta‐1,3‐diene and Allenic Esters: An Efficient Route to Novel 6‐Alkylidene‐6H‐2‐phenyl‐5‐ethoxycarbonyl‐1,3‐thiazines.

1,3-Thiazines and their Benzo Derivatives

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